Squarylium compounds and infrared cut films, infrared cut filters and electronic devices including the same

ABSTRACT

A squarylium compound has high transmittance in a visible wavelength spectrum of light and is configured to selectively absorb light in an infrared/near infrared wavelength spectrum of light.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims priority to and the benefit of, under 35 U.S.C.§ 119, Korean Patent Application No. 10-2017-0041844 filed in the KoreanIntellectual Property Office on Mar. 31, 2017, the entire contents ofwhich are incorporated herein by reference.

BACKGROUND 1. Field

A squarylium compound and infrared cut films, infrared cut filters, andelectronic devices including the same are disclosed.

2. Description of the Related Art

A display device may display a color image based on emitting light of acombination of three primary colors of red, blue, and green. In somecases, in order to be configured to provide an image having a cleartone, a display device may include a color filter having a colorcorrection function. Such a filter having a color correction functionmay be an infrared/near infrared cut filter configured to selectivelytransmit or cut light in a certain wavelength spectrum of light, oflight passing through the filter. Such light passing through the filtermay include light emitted by one or more portions of the display device.

Such infrared/near infrared cut filters have been manufactured accordingto various methods. For example, there is a method of depositing a metalsuch as silver on a surface of a transparent substrate such as glass, sothat the deposited metal may reflect a near infrared ray. Another methodmay include adding a near infrared ray absorption dye to a transparentresin such as an acrylic resin or a polycarbonate resin.

In some cases, an infrared/near infrared cut filter manufactured bydepositing a metal on a glass substrate may include foreign particlesmixed therein. Such foreign particles may include, for example, glasspieces of the glass substrate.

Accordingly, there are needs for development of an absorption dye havingimproved near infrared ray absorption performance.

SUMMARY

Some example embodiments provide a squarylium compound having hightransmittance in a visible wavelength spectrum of light and capable ofselectively absorbing light in an infrared/near infrared wavelengthspectrum of light.

Some example embodiments provide an infrared cut film and an infraredcut filter including the squarylium compound.

Yet some example embodiments provide an electronic device including thesquarylium compound.

According to some example embodiments, a squarylium compound representedby Chemical Formula 1 is provided.

In Chemical Formula 1, X¹ and X² are the same or different and are eachindependently one of a functional group represented by Chemical Formula1A, a functional group represented by Chemical Formula 1B, a functionalgroup represented by Chemical Formula 1C, and a functional grouprepresented by Chemical Formula 1D, provided that at least one of X¹ andX² is a functional group represented by Chemical Formula 1A or afunctional group represented by Chemical Formula 1B,

wherein, in Chemical Formula 1A,

Y¹ and Y² are independently N or NR¹⁶,

R¹¹ and R¹² are linked with each other to collectively comprise a fusedring with a quinazoline ring, or R¹¹ and R¹² are each independently onecompound of a first set of compounds, the first set of compoundsincluding hydrogen, a halogen, a cyano group, a nitro group, a hydroxylgroup, a carboxyl group, an ester group, a substituted or unsubstitutedC1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxygroup, a substituted or unsubstituted C6 to C30 aryl group, asubstituted or unsubstituted C3 to C20 cycloalkyl group, a substitutedor unsubstituted C3 to C20 heteroaryl group, and a substituted orunsubstituted C2 to C20 heterocycloalkyl group,

R¹³ is one compound of a second set of compounds, the second set ofcompounds including a substituted or unsubstituted C6 to C30 aryl group,a substituted or unsubstituted C3 to C20 heteroaryl group, a substitutedor unsubstituted C6 to C20 arylamine group, and a substituted orunsubstituted C3 to C30 heteroarylamine group, and

R¹⁴ and R¹⁵ are linked with each other to collectively comprise a fusedring with a quinazoline ring, or R¹⁴, R¹⁵, and R¹⁶ are independently onecompound of the first set of compounds,

wherein, in Chemical Formula 1B,

m is 1 or 2,

Z¹ and Z² are independently one of hydrogen or a hydroxyl group,

R²¹ to R²⁶ are independently one compound of the first set of compounds,and

R²⁷ and R²⁸ are linked with each other to collectively comprise anN-containing aromatic ring group or an N-containing alicyclic cyclicgroup, or R²⁷ and R²⁸ are independently one compound of a third set ofcompounds, the third set of compounds including a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1to C20 alkoxy group, a substituted or unsubstituted C6 to C30 arylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 heteroaryl group, and asubstituted or unsubstituted C2 to C20 heterocycloalkyl group,

wherein, in Chemical Formula 1C,

n is 1 or 2,

R³¹ and R³² are linked with each other to collectively comprise anaromatic ring group or an alicyclic cyclic group,

R³³ and R³⁴ are linked with each other to collectively comprise anaromatic ring group or an alicyclic cyclic group, and

R³⁵ to R³⁸ are independently one compound of the first set of compounds,

wherein, in Chemical Formula 1D,

k is 0 or 1,

Z³ and Z⁴ are independently one of hydrogen or a hydroxyl group,

R⁴¹ and R⁴² are independently one compound of the first set ofcompounds, and

R⁴³ and R⁴⁴ are linked with each other to collectively comprise anN-containing aromatic ring group or an N-containing alicyclic cyclicgroup, or R⁴³ and R⁴⁴ are independently one of a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1to C20 alkoxy group, a substituted or unsubstituted C6 to C30 arylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 heteroaryl group, and asubstituted or unsubstituted C2 to C20 heterocycloalkyl group.

R¹¹ and R¹² of Chemical Formula 1A may be linked with each other tocollectively comprise a C6 or C7 aromatic ring fused with a quinazolinering and the aromatic ring may not include a heteroatom.

The functional group represented by Chemical Formula 1A may be afunctional group represented by Chemical Formula 1A-1.

In Chemical Formula 1A-1,

Y¹ and Y² are independently N or NR¹⁶,

R¹⁶, R¹⁷, R¹⁸, and R¹⁹ are one of N or NR¹⁶, wherein R¹⁶ is one ofhydrogen or a substituted or unsubstituted C1 to C6 alkyl group, R¹⁷,R¹⁸, and R¹⁹ are independently one compound of the first set ofcompounds,

R¹³ is one compound of the second set of compounds, and

R¹⁴ and R¹⁵ are linked with each other to collectively comprise a ringfused with a quinazoline ring, or R¹⁴ and R¹⁵ are independently onecompound of the first set of compounds.

R¹³ of Chemical Formula 1A or Chemical Formula 1A-1 may be selected froma substituted or unsubstituted phenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted anthracenylgroup, a substituted or unsubstituted phenanthrenyl group, a substitutedor unsubstituted pyrenyl group, a substituted or unsubstituted chrysenylgroup, a substituted or unsubstituted fluorenyl group, and a substitutedor unsubstituted perylenyl group.

R¹³ of Chemical Formula 1A or Chemical Formula 1A-1 may be selected froma substituted or unsubstituted pyridyl group, a substituted orunsubstituted pyrazinyl group, a substituted or unsubstitutedpyrimidinyl group, a substituted or unsubstituted pyridazinyl group, asubstituted or unsubstituted quinolyl group, a substituted orunsubstituted isoquinolyl group, a substituted or unsubstitutedphthalazinyl group, a substituted or unsubstituted quinazolinyl group, asubstituted or unsubstituted quinoxalinyl group, a substituted orunsubstituted naphthyridinyl group, a substituted or unsubstitutedcinnolinyl group, a substituted or unsubstituted pyrrolyl group, asubstituted or unsubstituted pyrazolyl group, a substituted orunsubstituted imidazolyl group, a substituted or unsubstituted triazolylgroup, a substituted or unsubstituted tetrazolyl group, a substituted orunsubstituted thienyl group, a substituted or unsubstituted thiazolylgroup, a substituted or unsubstituted oxazolyl group, a substituted orunsubstituted indolyl group, a substituted or unsubstituted isoindolylgroup, a substituted or unsubstituted indazolyl group, a substituted orunsubstituted benzoimidazolyl group, a substituted or unsubstitutedbenzotriazolyl group, a substituted or unsubstituted benzothiazolylgroup, a substituted or unsubstituted benzooxazolyl group, a substitutedor unsubstituted carbazole group, a substituted or unsubstitutedphenazinyl group, and a substituted or unsubstituted acridinyl group.

R¹³ of Chemical Formula 1A or Chemical Formula 1A-1 may be onefunctional group of a plurality of functional groups represented byChemical Formula 2.

In Chemical Formula 2,

hydrogen of each aromatic ring may be replaced by a substituent selectedfrom a halogen, a cyano group, a nitro group, a hydroxyl group, acarboxyl group, an ester group, a substituted or unsubstituted C1 to C20alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, asubstituted or unsubstituted C6 to C30 aryl group, a substituted orunsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstitutedC3 to C20 heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group, and

each position of a plurality of aromatic rings of the plurality offunctional groups that is not indicated by an asterisk (*) is a bindingposition at R¹³ of Chemical Formula 1A.

R¹³ of Chemical Formula 1A or Chemical Formula 1A-1 may be selected froma substituted or unsubstituted pyrrolidinyl group, a substituted orunsubstituted piperidinyl group, a substituted or unsubstitutedpiperazinyl group, a substituted or unsubstituted morpholinyl group, asubstituted or unsubstituted thiomorpholinyl group, a substituted orunsubstituted tetrahydropyridyl group, a substituted or unsubstitutedtetrahydroquinolinyl group, a substituted or unsubstitutedtetrahydroisoquinolinyl group, a substituted or unsubstitutedtetrahydrofuryl group, a substituted or unsubstituted tetrahydropyranylgroup, a substituted or unsubstituted dihydrobenzofuranyl group, asubstituted or unsubstituted indolinyl group, a substituted orunsubstituted isoindolinyl group, and a substituted or unsubstitutedtetrahydrocarbazolyl group.

In R¹³ of Chemical Formula 1A or Chemical Formula 1A-1, the substitutedor unsubstituted C6 to C20 arylamine group and the substituted orunsubstituted C3 to C30 heteroarylamine group may be represented by—NR^(x)R^(y) wherein R^(x) and R^(y) are independently selected from asubstituted or unsubstituted C6 to C30 aryl group and a substituted orunsubstituted C3 to C20 heteroaryl group.

Chemical Formula 1B may be one functional group of a plurality offunctional groups represented by Chemical Formula 1B-1, Chemical Formula1B-2, and Chemical Formula 1B-3.

In Chemical Formula 1B-1,

m is 1 or 2,

Z¹ and Z² are independently hydrogen or a hydroxyl group,

R²¹ to R²⁶ are independently one compound of the first set of compounds,

R^(a) and R^(b) are independently one compound of the first set ofcompounds, and

a and b are independently an integer that is inclusively between 0 to 5.

In Chemical Formula 1B-2,

m is 1 or 2,

Z¹ and Z² are independently one of hydrogen or a hydroxyl group,

R²¹ to R²⁶ are independently one compound of the first set of compounds,

R^(a) and R^(b) are independently one compound of the first set ofcompounds, and

a and b are independently an integer that is inclusively between 0 to 4.

In Chemical Formula 1B-3,

m is 1 or 2,

Z¹ and Z² are independently one of hydrogen or a hydroxyl group,

R²¹ to R²⁶ are independently one compound of the first set of compounds,

R^(a) and R^(b) are independently one compound of the first set ofcompounds,

Y is selected from (“one of”) NR^(c), O, S, Se, and Te (wherein R^(c) isselected from hydrogen and a substituted or unsubstituted C1 to C6 alkylgroup), and

a and b are independently an integer that is inclusively between 0 to 4.

Chemical Formula 1C may be selected from functional groups representedby Chemical Formulae 1C-1 and 1C-2.

In Chemical Formula 1C-1 and Chemical Formula 1C-2,

R^(a), R^(b), R^(c), and R^(d) are independently one compound of thefirst set of compounds,

a and b are independently an integer that is inclusively between 0 to 6,

c is an integer that is inclusively between 0 to 2, and

e is an integer that is inclusively between 0 to 3.

Chemical Formula 1D may be one functional group of a plurality offunctional groups represented by Chemical Formula 1D-1, Chemical Formula1D-2, and Chemical Formula 1D-3.

In Chemical Formula 1D-1,

k is 0 or 1,

Z³ and Z⁴ are independently one of hydrogen or a hydroxyl group,

R⁴¹ and R⁴² are independently one compound of the first set ofcompounds,

R^(a) and R^(b) are independently one compound of the first set ofcompounds, and

a and b are independently an integer that is inclusively between 0 to 5.

In Chemical Formula 1D-2 and Chemical Formula 1D-3,

k is 0 or 1,

Z³ and Z⁴ are independently one of hydrogen or a hydroxyl group,

R⁴¹ and R⁴² are independently one compound of the first set ofcompounds,

R^(a) and R^(b) are independently one compound of the first set ofcompounds,

Y is one of NR^(c), O, S, Se, and Te (wherein R^(c) is selected fromhydrogen and a substituted or unsubstituted C1 to C6 alkyl group), and

a and b are independently an integer that is inclusively between 0 to 4.

The squarylium compound may be a particular compound represented by onechemical formula of Chemical Formula 4-1, Chemical Formula 4-2, ChemicalFormula 4-3, Chemical Formula 4-4, Chemical Formula 4-5, ChemicalFormula 4-6, Chemical Formula 4-7, Chemical Formula 4-8, ChemicalFormula 4-9, and Chemical Formula 4-10.

In Chemical Formula 4-1,

R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(14′), R^(15′), R^(16′), R^(17′),R^(18′), R^(19′), R^(p), and R^(p′) are independently one compound ofthe first set of compounds, and p and p′ are independently an integerthat is inclusively between 0 to 4.

In Chemical Formula 4-2,

R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(14′), R^(15′), R^(16′), R^(17′),R^(18′), R^(19′), R^(p), R^(p′), R^(q), and R^(q′) are independently onecompound of the first set of compounds, p and p′ are independently aninteger that is inclusively between 0 to 4, and q and q′ areindependently an integer that is inclusively between 0 to 2.

In Chemical Formula 4-3,

R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(14′), R^(15′), R^(16′), R^(17′),R^(18′), R^(19′), R^(p), R^(p′), R^(q), and R^(q′) are independently onecompound of the first set of compounds, and p and p′ are independentlyan integer that is inclusively between 0 to 4.

In Chemical Formula 4-4,

R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(p), R^(r), and R^(s) are independentlyone compound of the first set of compounds, p is an integer that isinclusively between 0 to 4, and r and s are independently an integerthat is inclusively between 0 to 5.

In Chemical Formula 4-5,

R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(p), R^(q), R^(r), and R^(s) areindependently one compound of the first set of compounds, p is aninteger that is inclusively between 0 to 4, q is an integer that isinclusively between 0 to 2, and r and s are independently an integerthat is inclusively between 0 to 5.

In Chemical Formula 4-6,

R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(p), R^(q), R^(r), and R^(s) areindependently one compound of the first set of compounds, p is aninteger that is inclusively between 0 to 4, q is an integer that isinclusively between 0 to 2, and r and s are independently an integerthat is inclusively between 0 to 5.

In Chemical Formula 4-7,

R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(p), R^(q), R^(r), R^(s), and R^(w) areindependently one compound of the first set of compounds, p and w areindependently an integer that is inclusively between 0 to 4, and r and sare independently an integer that is inclusively between 0 to 5.

In Chemical Formula 4-8,

R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(p), R^(q), R^(r), R^(s), and R^(w) areindependently one compound of the first set of compounds, p and w areindependently an integer that is inclusively between 0 to 4, q is aninteger that is inclusively between 0 to 2, and r and s areindependently an integer that is inclusively between 0 to 5.

In Chemical Formula 4-9,

R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(p), R^(q), R^(r), R^(s), and R^(w) areindependently one compound of the first set of compounds, p and w areindependently an integer that is inclusively between 0 to 4, and r and sare independently an integer that is inclusively between 0 to 5.

In Chemical Formula 4-10,

R^(r), R^(s), R^(w), R^(r′), R^(s′), and R^(w′) are independently onecompound of the first set of compounds, w and w′ are independently aninteger that is inclusively between 0 to 4, and r, s, r′, and s′ areindependently an integer that is inclusively between 0 to 5.

The squarylium compound may be configured to have a maximum absorptionwavelength (λ_(max)) in a range of greater than or equal to about 700 nmand less than or equal to about 1300 nm based on the squarylium compoundbeing in a thin film state.

The squarylium compound may have a full width at half maximum (FWHM) ofat least about 50 nm and less than or equal to about 150 nm based on thesquarylium compound being in a thin film state.

The squarylium compound may be associated with a maximum absorptioncoefficient in an infrared ray (IR) wavelength spectrum of light(A_(NIR)) and a maximum absorption coefficient in a visible wavelengthspectrum of light (A_(VIS)) that satisfy Relationship Equation 1A _(NIR) /A _(VIS)≥8  [Relationship Equation 1]

A ratio (A_(NIR)/A_(VIS)) of the absorption coefficients may be in arange of about 10 to about 550.

Some example embodiments provide an infrared cut film including thesquarylium compound.

Some example embodiments provide the infrared cut film and an infraredlight reflection layer on at least one surface of the infrared cut film.

The infrared light reflection layer may include an inorganicparticulate, and may be a multi-layered thin film including a firstdeposition film of an inorganic particulate that is at least oneparticulate of titania (TiO₂), zirconia, and a combination thereof and asecond deposition film of an inorganic particulate that is at least oneparticulate of silica (SiO₂), alumina, and a combination thereof.

A thickness of the infrared cut film may be in a range of about 50 μm toabout 200 μm.

Some example embodiments provide an electronic device including thesquarylium compound.

Some example embodiments provide an electronic device including theinfrared cut film.

The electronic device may be an image sensor including a firstphoto-sensing device configured to sense light in a blue wavelengthspectrum of light, a second photo-sensing device configured to senselight in a red wavelength spectrum of light, a third photo-sensingdevice configured to sense light in a green wavelength spectrum oflight, and a fourth photo-sensing device configured to sense light in aninfrared/near infrared wavelength spectrum of light, wherein the fourthphoto-sensing device includes the squarylium compound.

The fourth photo-sensing device may be disposed on the firstphoto-sensing device, the second photo-sensing device, and the thirdphoto-sensing device, wherein at least two of the first photo-sensingdevice, the second photo-sensing device, and the third photo-sensingdevice may be stacked.

The first photo-sensing device and the second photo-sensing device mayextend in parallel to each other, the third photo-sensing device may bedisposed on the first photo-sensing device and the second photo-sensingdevice, and the fourth photo-sensing device may be disposed on the thirdphoto-sensing device.

The image sensor may include a blue filter configured to selectivelyabsorb light in a blue wavelength spectrum of light on the firstphoto-sensing device, a red filter configured to selectively absorblight in a blue wavelength spectrum of light on the second photo-sensingdevice, a green filter configured to selectively absorb light in a bluewavelength spectrum of light on the third photo-sensing device, and aninfrared cut filter configured to selectively absorb light in aninfrared/near infrared wavelength spectrum of light on the fourthphoto-sensing device.

The infrared cut filter may be on the blue filter, the red filter, andthe green filter.

The squarylium compound may have (e.g., may be associated with) lowabsorbance in a visible wavelength spectrum of light and high absorbancein an infrared/near infrared wavelength spectrum of light, and thus maybe configured to have improved spectral sensitivity at low illuminationand may be applied to various electronic devices to thus improvespectral sensitivity thereof in low illumination environments.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a schematic cross-sectional view of an infrared cut filteraccording to some example embodiments.

FIG. 2 is a schematic cross-sectional view of an infrared cut filteraccording to some example embodiments.

FIGS. 3 to 18 are schematic cross-sectional views of image sensorsaccording to some example embodiments.

FIG. 19 is a block diagram of a digital camera including an image sensoraccording to some example embodiments.

FIG. 20 is a graph showing absorbance depending on a wavelength ofCompound A obtained in Synthesis Example 1.

FIG. 21 is a graph showing absorbance depending on a wavelength ofCompound Q obtained in Synthesis Example 16.

FIG. 22 is a graph showing absorbance depending on a wavelength ofCompound R obtained in Synthesis Example 17.

FIG. 23 is a graph showing absorbance depending on a wavelength ofCompound T obtained in Comparative Synthesis Example 1.

FIG. 24 is a graph showing absorbance depending on a wavelength ofCompound U obtained in Comparative Synthesis Example 2.

FIG. 25 is a graph showing absorbance depending on a wavelength ofCompound V obtained in Comparative Synthesis Example 3.

FIG. 26 is a graph showing absorbance depending on a wavelength ofCompound W obtained in Comparative Synthesis Example 4.

DETAILED DESCRIPTION

Hereinafter, example embodiments will be described in detail, and may beeasily performed by a person having an ordinary skill in the relatedart. However, this disclosure may be embodied in many different formsand is not construed as limited to the example embodiments set forthherein.

It should be understood that, although the terms first, second, third,etc. may be used herein to describe various elements, components,regions, layers and/or sections, these elements, components, regions,layers, and/or sections should not be limited by these terms. Theseterms are only used to distinguish one element, component, region,layer, or section from another region, layer, or section. Thus, a firstelement, component, region, layer, or section discussed below could betermed a second element, component, region, layer, or section withoutdeparting from the teachings of example embodiments.

Spatially relative terms (e.g., “beneath,” “below,” “lower,” “above,”“upper,” and the like) may be used herein for ease of description todescribe one element or feature's relationship to another element(s) orfeature(s) as illustrated in the figures. It should be understood thatthe spatially relative terms are intended to encompass differentorientations of the device in use or operation in addition to theorientation depicted in the figures. For example, if the device in thefigures is turned over, elements described as “below” or “beneath” otherelements or features would then be oriented “above” the other elementsor features. Thus, the term “below” may encompass both an orientation ofabove and below. The device may be otherwise oriented (rotated 90degrees or at other orientations) and the spatially relative descriptorsused herein interpreted accordingly.

The terminology used herein is for the purpose of describing variousembodiments only and is not intended to be limiting of exampleembodiments. As used herein, the singular forms “a,” “an,” and “the” areintended to include the plural forms as well, unless the context clearlyindicates otherwise. It will be further understood that the terms“includes,” “including,” “comprises,” and/or “comprising,” when used inthis specification, specify the presence of stated features, integers,steps, operations, elements, and/or components, but do not preclude thepresence or addition of one or more other features, integers, steps,operations, elements, components, and/or groups thereof.

Example embodiments are described herein with reference tocross-sectional illustrations that are schematic illustrations ofidealized embodiments (and intermediate structures) of exampleembodiments. As such, variations from the shapes of the illustrations asa result, for example, of manufacturing techniques and/or tolerances,are to be expected. Thus, example embodiments should not be construed aslimited to the shapes of regions illustrated herein but are to includedeviations in shapes that result, for example, from manufacturing.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which example embodiments belong. Itwill be further understood that terms, including those defined incommonly used dictionaries, should be interpreted as having a meaningthat is consistent with their meaning in the context of the relevant artand will not be interpreted in an idealized or overly formal senseunless expressly so defined herein.

As used herein, when a definition is not otherwise provided, “infraredlight” refers to “near infrared light (NIR)” in a region of about 700 nmto about 1400 nm.

When the terms “about” or “substantially” are used in this specificationin connection with a numerical value, it is intended that the associatednumerical value include a tolerance of ±10% around the stated numericalvalue. When ranges are specified, the range includes all valuestherebetween such as increments of 0.1%.

As used herein, when a definition is not otherwise provided,“substituted” refers to replacement of hydrogen of a compound or afunctional group by a substituent selected from a halogen (F, Br, Cl, orI), a hydroxy group, a nitro group, a cyano group, an amino group, anazido group, an amidino group, a hydrazino group, a hydrazono group, acarbonyl group, a carbamyl group, a thiol group, an ester group, acarboxyl group or a salt thereof, a sulfonic acid group or a saltthereof, a phosphoric acid or a salt thereof, a C1 to C20 alkyl group,for example a C1 to C10 alkyl group, a C1 to C20 alkoxy group, forexample a C1 to C10 alkoxy group, a C2 to C20 alkenyl group, a C2 to C20alkynyl group, a C6 to C30 aryl group, a C7 to C30 arylalkyl group, a C3to C20 heteroaryl group, a C3 to C20 heteroarylalkyl group, a C3 to C30cycloalkyl group, a C3 to C15 cycloalkenyl group, a C6 to C15cycloalkynyl group, a C2 to C20 heterocycloalkyl group, and acombination thereof.

In addition, “substituted” in an aromatic ring group refers toreplacement of —CH₂— in the ring by —NR— (wherein R is selected fromhydrogen, a halogen, a C1 to C10 alkyl group, a C1 to C10 alkoxy group,a C6 to C30 aryl group, and a C3 to C20 heteroaryl group), —O—, —S—, or—Se— or replacement of —CH═ in the ring by —N═.

As used herein, when a definition is not otherwise provided, “hetero”refers to inclusion of one to three heteroatoms selected from N, O, S,P, and Si.

As used herein, when a definition is not otherwise provided, “halogen”refers to F, Br, Cl, or I.

Singular terms in the present disclosure may include a plurality ofobjects unless one object is precisely indicated.

All numerical ranges of the present disclosure include all numbers andranges within set forth numerical ranges. In addition, numerical rangesand parameters indicating a broad scope of this disclosure areapproximate values but the numerical values set forth in the Examplessection are reported as precisely as possible. However, it should beunderstood that such numerical values inherently contain certain errorsresulting from measuring equipment and/or a measuring technique.

According to some example embodiments, a squarylium compound representedby Chemical Formula 1 is provided.

In Chemical Formula 1, X¹ and X² are the same or different and areindependently selected from a functional group represented by ChemicalFormula 1A, a functional group represented by Chemical Formula 1B, afunctional group represented by Chemical Formula 1C, and a functionalgroup represented by Chemical Formula 1D, provided that at least one ofX¹ and X² is a functional group represented by Chemical Formula 1A or afunctional group represented by Chemical Formula 1B,

wherein, in Chemical Formula 1A,

Y¹ and Y² are independently N or NR¹⁶,

R¹¹ and R¹² are independently one compound of a first set of compounds,where the first set of compounds includes hydrogen, a halogen, a cyanogroup, a nitro group, a hydroxyl group, a carboxyl group, an estergroup, a substituted or unsubstituted C1 to C20 alkyl group, asubstituted or unsubstituted C1 to C20 alkoxy group, a substituted orunsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 toC20 cycloalkyl group, a substituted or unsubstituted C3 to C20heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group, or R¹¹ and R¹² are linked with each other tocollectively comprise a fused ring with a quinazoline ring,

R¹³ is one compound of a second set of compounds, the second set ofcompounds including a substituted or unsubstituted C6 to C30 aryl group,a substituted or unsubstituted C3 to C20 heteroaryl group, a substitutedor unsubstituted C6 to C20 arylamine group, and a substituted orunsubstituted C3 to C30 heteroarylamine group, and

R¹⁴, R¹⁵, and R¹⁶ are independently selected from (“independently oneof”) hydrogen, a halogen, a cyano group, a nitro group, a hydroxylgroup, a carboxyl group, an ester group, a substituted or unsubstitutedC1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxygroup, a substituted or unsubstituted C6 to C30 aryl group, asubstituted or unsubstituted C3 to C20 cycloalkyl group, a substitutedor unsubstituted C3 to C20 heteroaryl group, and a substituted orunsubstituted C2 to C20 heterocycloalkyl group or R¹⁴ and R¹⁵ are linkedwith each other to provide a fused ring with a quinazoline ring,

wherein, in Chemical Formula 1B,

m is 1 or 2,

Z¹ and Z² are independently hydrogen or a hydroxyl group,

R²¹ to R²⁶ are independently selected from hydrogen, a halogen, a cyanogroup, a nitro group, a hydroxyl group, a carboxyl group, an estergroup, a substituted or unsubstituted C1 to C20 alkyl group, asubstituted or unsubstituted C1 to C20 alkoxy group, a substituted orunsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 toC20 cycloalkyl group, a substituted or unsubstituted C3 to C20heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group, and

R²⁷ and R²⁸ are independently selected from a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1to C20 alkoxy group, a substituted or unsubstituted C6 to C30 arylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 heteroaryl group, and asubstituted or unsubstituted C2 to C20 heterocycloalkyl group or R²⁷ andR²⁸ are optionally linked with each other to provide (“collectivelycomprise”) an N-containing aromatic ring group or an N-containingalicyclic cyclic group,

wherein, in Chemical Formula 1C,

n is 1 or 2,

R³¹ and R³² are linked with each other to provide an aromatic ring groupor an alicyclic cyclic group,

R³³ and R³⁴ are linked with each other to provide an aromatic ring groupor an alicyclic cyclic group, and

R³⁵ to R³⁸ are independently selected from hydrogen, a halogen, a cyanogroup, a nitro group, a hydroxyl group, a carboxyl group, an estergroup, a substituted or unsubstituted C1 to C20 alkyl group, asubstituted or unsubstituted C1 to C20 alkoxy group, a substituted orunsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 toC20 cycloalkyl group, a substituted or unsubstituted C3 to C20heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group,

wherein, in Chemical Formula 1D,

k is 0 or 1,

Z³ and Z⁴ are independently hydrogen or a hydroxyl group,

R⁴¹ and R⁴² are independently selected from hydrogen, a halogen, a cyanogroup, a nitro group, a hydroxyl group, a carboxyl group, an estergroup, a substituted or unsubstituted C1 to C20 alkyl group, asubstituted or unsubstituted C1 to C20 alkoxy group, a substituted orunsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 toC20 cycloalkyl group, a substituted or unsubstituted C3 to C20heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group, and

R⁴³ and R⁴⁴ are independently selected from a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1to C20 alkoxy group, a substituted or unsubstituted C6 to C30 arylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 heteroaryl group, and asubstituted or unsubstituted C2 to C20 heterocycloalkyl group or R⁴³ andR⁴⁴ are optionally linked with each other to provide an N-containingaromatic ring group or an N-containing alicyclic cyclic group.

The squarylium compound represented by Chemical Formula 1 may be acompound represented by Chemical Formula 1′.

The squarylium compound represented by Chemical Formula 1 includes anelectron donating group selected from the functional group representedby Chemical Formula 1A, the functional group represented by ChemicalFormula 1B, the functional group represented by Chemical Formula 1C, andthe functional group represented by Chemical Formula 1D in the center ofthe squarylium nucleus and at least one of X¹ and X² includes thefunctional group represented by Chemical Formula 1A or the functionalgroup represented by Chemical Formula 1B, and thereby the squaryliumcompound has excellent absorbance in an infrared/near infraredwavelength spectrum of light.

The squarylium compound may have (“be configured to have”) a maximumabsorption wavelength (λ_(max)) in a range of greater than or equal toabout 700 nm and less than or equal to about 1300 nm, for examplegreater than or equal to about 710 nm and less than or equal to about1200 nm and a full width at half maximum (FWHM) of greater than or equalto about 50 nm and less than or equal to about 150 nm, for examplegreater than or equal to about 50 nm and less than or equal to about 130nm, based on the squarylium compound being in a thin film state (e.g.,being included in a thin film).

The squarylium compound represented by Chemical Formula 1 has highabsorbance in an infrared/near infrared wavelength spectrum of light andhigh transmittance in a visible ray region and thereby high selectiveabsorbance in an infrared/near infrared wavelength spectrum of light.That is, the squarylium compound may be associated with a maximumabsorption coefficient in an infrared ray (IR) wavelength spectrum oflight (A_(NIR)) and a maximum absorption coefficient in a visiblewavelength spectrum of light (A_(VIS)) that satisfy RelationshipEquation 1.A _(NIR) /A _(VIS)≥8  [Relationship Equation 1]

In Relationship Equation 1,

A_(NIR) is a maximum absorption coefficient in an infrared ray (IR)region and A_(VIS) is a maximum absorption coefficient in a visiblewavelength spectrum of light.

A ratio (A_(NIR)/A_(VIS)) of the maximum absorption coefficient in theinfrared ray (IR) and the maximum absorption coefficient in the visiblewavelength spectrum of light may be greater than or equal to about 9,for example about 10 to about 550 or about 15 to about 550. When theratio (A_(NIR)/A_(VIS)) of the absorption coefficients is within theranges, selective absorbance for light in an infrared/near infraredwavelength spectrum of light is improved.

Transmittance in a visible wavelength spectrum of light of thesquarylium compound represented by Chemical Formula 1 may be greaterthan or equal to about 80%, for example greater than or equal to about90%, and particularly transmittance in a blue wavelength spectrum oflight of about 300 nm to about 450 nm may be greater than or equal toabout 80%, for example greater than or equal to about 90%. In addition,a molar extinction coefficient in an infrared/near infrared wavelengthspectrum of light may be greater than or equal to about 7×10⁴ M⁻¹cm⁻¹,for example greater than or equal to about 7.5×10⁴ M⁻¹ cm⁻¹, or greaterthan or equal to about 8×10⁴ M⁻¹ cm⁻¹. If absorbance in a bluewavelength spectrum of light of about 300 nm to about 450 nm is highdespite high absorbance in an infrared ray (IR) region, efficiency maybe deteriorated. From this view, the squarylium compound represented byChemical Formula 1 has low absorbance (i.e., high transmittance) in ablue wavelength spectrum of light of about 300 nm to about 450 nm andhigh absorbance in an infrared ray (IR) region, and thus efficiency(e.g., external quantum efficiency) of an electronic device may beimproved based on including the squarylium compound represented byChemical Formula 1.

R¹¹ and R¹² represented by Chemical Formula 1A are linked with eachother to provide a C6 or C7 aromatic ring that is fused with a fusedring (e.g., a quinazoline ring) of a 6-membered aromatic ring includingY¹ and Y² and a benzene ring and the aromatic ring may not include aheteroatom. In this case, a structure where three aromatic rings arefused structure is provided.

Chemical Formula 1A may be represented by Chemical Formula 1A-1.

In Chemical Formula 1A-1,

Y¹ and Y² are independently N or NR¹⁶,

R¹⁶, R¹⁷, R¹⁸, and R¹⁹ are independently selected from hydrogen, ahalogen, a cyano group, a nitro group, a hydroxyl group, a carboxylgroup, an ester group, a substituted or unsubstituted C1 to C20 alkylgroup, a substituted or unsubstituted C1 to C20 alkoxy group, asubstituted or unsubstituted C6 to C30 aryl group, a substituted orunsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstitutedC3 to C20 heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group,

R¹³ is a substituted or unsubstituted C6 to C30 aryl group, asubstituted or unsubstituted C3 to C20 heteroaryl group, a substitutedor unsubstituted C6 to C20 arylamine group, and a substituted orunsubstituted C3 to C30 heteroarylamine group, and

R¹⁴ and R¹⁵ are independently selected from hydrogen, a halogen, a cyanogroup, a nitro group, a hydroxyl group, a carboxyl group, an estergroup, a substituted or unsubstituted C1 to C20 alkyl group, asubstituted or unsubstituted C1 to C20 alkoxy group, a substituted orunsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 toC20 cycloalkyl group, a substituted or unsubstituted C3 to C20heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group or R¹⁴ and R¹⁵ are linked with each other toprovide a ring fused with a quinazoline ring.

R¹³ represented by Chemical Formula 1A or Chemical Formula 1A-1 may beselected from a substituted or unsubstituted phenyl group, a substitutedor unsubstituted naphthyl group, a substituted or unsubstitutedanthracenyl group, a substituted or unsubstituted phenanthrenyl group, asubstituted or unsubstituted pyrenyl group, a substituted orunsubstituted chrysenyl group, a substituted or unsubstituted fluorenylgroup, and a substituted or unsubstituted perylenyl group.

R¹³ represented by Chemical Formula 1A or Chemical Formula 1A-1 may beselected from a substituted or unsubstituted pyridyl group, asubstituted or unsubstituted pyrazinyl group, a substituted orunsubstituted pyrimidinyl group, a substituted or unsubstitutedpyridazinyl group, a substituted or unsubstituted quinolyl group, asubstituted or unsubstituted isoquinolyl group, a substituted orunsubstituted phthalazinyl group, a substituted or unsubstitutedquinazolinyl group, a substituted or unsubstituted quinoxalinyl group, asubstituted or unsubstituted naphthyridinyl group, a substituted orunsubstituted cinnolinyl group, a substituted or unsubstituted pyrrolylgroup, a substituted or unsubstituted pyrazolyl group, a substituted orunsubstituted imidazolyl group, a substituted or unsubstituted triazolylgroup, a substituted or unsubstituted tetrazolyl group, a substituted orunsubstituted thienyl group, a substituted or unsubstituted thiazolylgroup, a substituted or unsubstituted oxazolyl group, a substituted orunsubstituted indolyl group, a substituted or unsubstituted isoindolylgroup, a substituted or unsubstituted indazolyl group, a substituted orunsubstituted benzoimidazolyl group, a substituted or unsubstitutedbenzotriazolyl group, a substituted or unsubstituted benzothiazolylgroup, a substituted or unsubstituted benzooxazolyl group, a substitutedor unsubstituted carbazole group, a substituted or unsubstitutedphenazinyl group, and a substituted or unsubstituted acridinyl group.

R¹³ represented by Chemical Formula 1A or Chemical Formula 1A-1 may beone functional group of a plurality of functional groups represented byChemical Formula 2.

In Chemical Formula 2,

hydrogen of each aromatic ring may be replaced by a substituent selectedfrom a halogen, a cyano group, a nitro group, a hydroxyl group, acarboxyl group, an ester group, a substituted or unsubstituted C1 to C20alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, asubstituted or unsubstituted C6 to C30 aryl group, a substituted orunsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstitutedC3 to C20 heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group, and

each position of a plurality of aromatic rings of the plurality offunctional groups that is not indicated by an asterisk (*) may be abinding position at R¹³ of Chemical Formula 1A.

R¹³ represented by Chemical Formula 1A or Chemical Formula 1A-1 may be asubstituted or unsubstituted pyrrolidinyl group, a substituted orunsubstituted piperidinyl group, a substituted or unsubstitutedpiperazinyl group, a substituted or unsubstituted morpholinyl group, asubstituted or unsubstituted thiomorpholinyl group, a substituted orunsubstituted tetrahydropyridyl group, a substituted or unsubstitutedtetrahydroquinolinyl group, a substituted or unsubstitutedtetrahydroisoquinolinyl group, a substituted or unsubstitutedtetrahydrofuryl group, a substituted or unsubstituted tetrahydropyranylgroup, a substituted or unsubstituted dihydrobenzofuranyl group, asubstituted or unsubstituted indolinyl group, a substituted orunsubstituted isoindolinyl group, and a substituted or unsubstitutedtetrahydrocarbazolyl group which are represented by Chemical Formula 3.

In Chemical Formula 3,

R^(a) and R^(b) are independently selected from a halogen, a cyanogroup, a nitro group, a hydroxyl group, a carboxyl group, an estergroup, a substituted or unsubstituted C1 to C20 alkyl group, asubstituted or unsubstituted C1 to C20 alkoxy group, a substituted orunsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 toC20 cycloalkyl group, a substituted or unsubstituted C3 to C20heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group,

hydrogen of each aromatic ring or alicyclic ring may be replaced by asubstituent selected from a halogen, a cyano group, a nitro group, ahydroxyl group, a carboxyl group, an ester group, a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1to C20 alkoxy group, a substituted or unsubstituted C6 to C30 arylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 heteroaryl group, and asubstituted or unsubstituted C2 to C20 heterocycloalkyl group, and

any position of aromatic rings or alicyclic rings of functional groupsthat are not indicated by asterisk (*) may be a binding position at R¹³represented by Chemical Formula 1A or 1A-1.

In R¹³ represented by Chemical Formula 1A or Chemical Formula 1A-1, thesubstituted or unsubstituted C6 to C20 arylamine group and thesubstituted or unsubstituted C3 to C30 heteroarylamine group may berepresented by —NR^(x)R^(y) wherein R^(x) and R^(y) are independentlyselected from a substituted or unsubstituted C6 to C30 aryl group and asubstituted or unsubstituted C3 to C20 heteroaryl group.

In addition, the functional group represented by Chemical Formula 1B mayimprove selective absorbance in an infrared/near infrared wavelengthspectrum of light by further including a phenylene ring in front of anamine group.

The functional group represented by Chemical Formula 1B may be onefunctional group of a plurality of functional groups represented byChemical Formula 1B-1, Chemical Formula 1B-2, and Chemical Formula 1B-3.

In Chemical Formula 1B-1,

m is 1 or 2,

Z¹ and Z² are independently hydrogen or a hydroxyl group,

R²¹ to R²⁶ are independently selected from hydrogen, a halogen, a cyanogroup, a nitro group, a hydroxyl group, a carboxyl group, an estergroup, a substituted or unsubstituted C1 to C20 alkyl group, asubstituted or unsubstituted C1 to C20 alkoxy group, a substituted orunsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 toC20 cycloalkyl group, a substituted or unsubstituted C3 to C20heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group,

R^(a) and R^(b) are independently selected from hydrogen, a halogen, acyano group, a nitro group, a hydroxyl group, a carboxyl group, an estergroup, a substituted or unsubstituted C1 to C20 alkyl group, asubstituted or unsubstituted C1 to C20 alkoxy group, a substituted orunsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 toC20 cycloalkyl group, a substituted or unsubstituted C3 to C20heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group, and

a and b are independently an integer that is inclusively between 0 to 5.

In Chemical Formula 1B-2,

m is 1 or 2,

Z¹ and Z² are independently hydrogen or a hydroxyl group,

R²¹ to R²⁶ are independently selected from hydrogen, a halogen, a cyanogroup, a nitro group, a hydroxyl group, a carboxyl group, an estergroup, a substituted or unsubstituted C1 to C20 alkyl group, asubstituted or unsubstituted C1 to C20 alkoxy group, a substituted orunsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 toC20 cycloalkyl group, a substituted or unsubstituted C3 to C20heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group,

R^(a) and R^(b) are independently selected from hydrogen, a halogen, acyano group, a nitro group, a hydroxyl group, a carboxyl group, an estergroup, a substituted or unsubstituted C1 to C20 alkyl group, asubstituted or unsubstituted C1 to C20 alkoxy group, a substituted orunsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 toC20 cycloalkyl group, a substituted or unsubstituted C3 to C20heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group, and

a and b are independently an integer that is inclusively between 0 to 4.

In Chemical Formula 1B-3,

m is 1 or 2,

Z¹ and Z² are independently hydrogen or a hydroxyl group,

R²¹ to R²⁶ are independently selected from hydrogen, a halogen, a cyanogroup, a nitro group, a hydroxyl group, a carboxyl group, an estergroup, a substituted or unsubstituted C1 to C20 alkyl group, asubstituted or unsubstituted C1 to C20 alkoxy group, a substituted orunsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 toC20 cycloalkyl group, a substituted or unsubstituted C3 to C20heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group,

R^(a) and R^(b) are independently selected from hydrogen, a halogen, acyano group, a nitro group, a hydroxyl group, a carboxyl group, an estergroup, a substituted or unsubstituted C1 to C20 alkyl group, asubstituted or unsubstituted C1 to C20 alkoxy group, a substituted orunsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 toC20 cycloalkyl group, a substituted or unsubstituted C3 to C20heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group,

Y is selected from NR^(c), O, S, Se, and Te (wherein R^(c) is selectedfrom hydrogen and a substituted or unsubstituted C1 to C6 alkyl group),and

a and b are independently an integer that is inclusively between 0 to 4.

Chemical Formula 1C may be selected from functional groups (“onefunctional group of a plurality of functional groups”) represented byChemical Formulae 1C-1 and 1C-2.

In Chemical Formula 1C-1 and Chemical Formula 1C-2,

R^(a), R^(b), R^(c), and R^(d) are independently selected from hydrogen,a halogen, a cyano group, a nitro group, a hydroxyl group, a carboxylgroup, an ester group, a substituted or unsubstituted C1 to C20 alkylgroup, a substituted or unsubstituted C1 to C20 alkoxy group, asubstituted or unsubstituted C6 to C30 aryl group, a substituted orunsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstitutedC3 to C20 heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group,

a and b are independently an integer that is inclusively between 0 to 6,

c is an integer that is inclusively between 0 to 2, and

e is an integer that is inclusively between 0 to 3.

Chemical Formula 1D may be selected from functional groups representedby Chemical Formula 1D-1, Chemical Formula 1D-2, and Chemical Formula1D-3.

In Chemical Formula 1D-1,

k is 0 or 1,

Z³ and Z⁴ are independently hydrogen or a hydroxyl group,

R⁴¹ and R⁴² are independently selected from hydrogen, a halogen, a cyanogroup, a nitro group, a hydroxyl group, a carboxyl group, an estergroup, a substituted or unsubstituted C1 to C20 alkyl group, asubstituted or unsubstituted C1 to C20 alkoxy group, a substituted orunsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 toC20 cycloalkyl group, a substituted or unsubstituted C3 to C20heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group,

R^(a) and R^(b) are independently selected from hydrogen, a halogen, acyano group, a nitro group, a hydroxyl group, a carboxyl group, an estergroup, a substituted or unsubstituted C1 to C20 alkyl group, asubstituted or unsubstituted C1 to C20 alkoxy group, a substituted orunsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 toC20 cycloalkyl group, a substituted or unsubstituted C3 to C20heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group, and

a and b are independently an integer that is inclusively between 0 to 5.

In Chemical Formula 1D-2 and Chemical Formula 1D-3,

k is 0 or 1,

Z³ and Z⁴ are independently hydrogen or a hydroxyl group,

R⁴¹ and R⁴² are independently selected from hydrogen, a halogen, a cyanogroup, a nitro group, a hydroxyl group, a carboxyl group, an estergroup, a substituted or unsubstituted C1 to C20 alkyl group, asubstituted or unsubstituted C1 to C20 alkoxy group, a substituted orunsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 toC20 cycloalkyl group, a substituted or unsubstituted C3 to C20heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group,

R^(a) and R^(b) are independently selected from hydrogen, a halogen, acyano group, a nitro group, a hydroxyl group, a carboxyl group, an estergroup, a substituted or unsubstituted C1 to C20 alkyl group, asubstituted or unsubstituted C1 to C20 alkoxy group, a substituted orunsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 toC20 cycloalkyl group, a substituted or unsubstituted C3 to C20heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group,

Y is selected from NR^(c), O, S, Se, and Te (wherein R^(c) is selectedfrom hydrogen and a substituted or unsubstituted C1 to C6 alkyl group),and

a and b are independently an integer that is inclusively between 0 to 4.

The squarylium compound may be a particular compound represented by onechemical formula represented by Chemical Formula 4-1, Chemical Formula4-2, Chemical Formula 4-3, Chemical Formula 4-4, Chemical Formula 4-5,Chemical Formula 4-6, Chemical Formula 4-7, Chemical Formula 4-8,Chemical Formula 4-9, and Chemical Formula 4-10.

In Chemical Formula 4-1,

R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(14′), R^(15′), R^(16′), R^(17′),R^(18′), R^(19′), R^(p), and R^(p′) are independently selected fromhydrogen, a halogen, a cyano group, a nitro group, a hydroxyl group, acarboxyl group, an ester group, a substituted or unsubstituted C1 to C20alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, asubstituted or unsubstituted C6 to C30 aryl group, a substituted orunsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstitutedC3 to C20 heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group, and p and p′ are independently an integer thatis inclusively between 0 to 4.

In Chemical Formula 4-2,

R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(14′), R^(15′), R^(16′), R^(17′),R^(18′), R^(19′), R^(p), R^(p′), R^(q), and R^(q′) are independentlyselected from hydrogen, a halogen, a cyano group, a nitro group, ahydroxyl group, a carboxyl group, an ester group, a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1to C20 alkoxy group, a substituted or unsubstituted C6 to C30 arylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 heteroaryl group, and asubstituted or unsubstituted C2 to C20 heterocycloalkyl group, p and p′are independently an integer that is inclusively between 0 to 4, and qand q′ are independently an integer that is inclusively between 0 to 2.

In Chemical Formula 4-3,

R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(14′), R¹⁵, R^(16′), R¹⁷, R¹⁸, R^(19′),R^(p), R^(p′), R^(q), and R^(q′) are independently selected fromhydrogen, a halogen, a cyano group, a nitro group, a hydroxyl group, acarboxyl group, an ester group, a substituted or unsubstituted C1 to C20alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, asubstituted or unsubstituted C6 to C30 aryl group, a substituted orunsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstitutedC3 to C20 heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group, and p and p′ are independently an integer thatis inclusively between 0 to 4.

In Chemical Formula 4-4,

R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(p), R^(r), and R^(s) are independentlyselected from hydrogen, a halogen, a cyano group, a nitro group, ahydroxyl group, a carboxyl group, an ester group, a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1to C20 alkoxy group, a substituted or unsubstituted C6 to C30 arylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 heteroaryl group, and asubstituted or unsubstituted C2 to C20 heterocycloalkyl group, p is aninteger that is inclusively between 0 to 4, and r and s areindependently an integer that is inclusively between 0 to 5.

In Chemical Formula 4-5,

R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(p), R^(q), R^(r), and R^(s) areindependently selected from hydrogen, a halogen, a cyano group, a nitrogroup, a hydroxyl group, a carboxyl group, an ester group, a substitutedor unsubstituted C1 to C20 alkyl group, a substituted or unsubstitutedC1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 arylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 heteroaryl group, and asubstituted or unsubstituted C2 to C20 heterocycloalkyl group, p is aninteger that is inclusively between 0 to 4, q is an integer that isinclusively between 0 to 2, and r and s are independently an integerthat is inclusively between 0 to 5.

In Chemical Formula 4-6,

R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(p), R^(q), R^(r), and R^(s) areindependently selected from hydrogen, a halogen, a cyano group, a nitrogroup, a hydroxyl group, a carboxyl group, an ester group, a substitutedor unsubstituted C1 to C20 alkyl group, a substituted or unsubstitutedC1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 arylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 heteroaryl group, and asubstituted or unsubstituted C2 to C20 heterocycloalkyl group, p is aninteger that is inclusively between 0 to 4, q is an integer that isinclusively between 0 to 2, and r and s are independently an integerthat is inclusively between 0 to 5.

In Chemical Formula 4-7,

R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(p), R^(q), R^(r), R^(s), and R^(w) areindependently selected from hydrogen, a halogen, a cyano group, a nitrogroup, a hydroxyl group, a carboxyl group, an ester group, a substitutedor unsubstituted C1 to C20 alkyl group, a substituted or unsubstitutedC1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 arylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 heteroaryl group, and asubstituted or unsubstituted C2 to C20 heterocycloalkyl group, p and ware independently an integer that is inclusively between 0 to 4, and rand s are independently an integer that is inclusively between 0 to 5.

In Chemical Formula 4-8,

R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(p), R^(q), R^(r), R^(s), and R^(w) areindependently selected from hydrogen, a halogen, a cyano group, a nitrogroup, a hydroxyl group, a carboxyl group, an ester group, a substitutedor unsubstituted C1 to C20 alkyl group, a substituted or unsubstitutedC1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 arylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 heteroaryl group, and asubstituted or unsubstituted C2 to C20 heterocycloalkyl group, p and ware independently an integer that is inclusively between 0 to 4, q is aninteger that is inclusively between 0 to 2, and r and s areindependently an integer that is inclusively between 0 to 5.

In Chemical Formula 4-9,

R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(p), R^(q), R^(r), R^(s), and R^(w) areindependently selected from hydrogen, a halogen, a cyano group, a nitrogroup, a hydroxyl group, a carboxyl group, an ester group, a substitutedor unsubstituted C1 to C20 alkyl group, a substituted or unsubstitutedC1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 arylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 heteroaryl group, and asubstituted or unsubstituted C2 to C20 heterocycloalkyl group, p and ware independently an integer that is inclusively between 0 to 4, and rand s are independently an integer that is inclusively between 0 to 5.

In Chemical Formula 4-10,

R^(r), R^(s), R^(w), R^(r′), R^(s′), and R^(w′) are independentlyselected from hydrogen, a halogen, a cyano group, a nitro group, ahydroxyl group, a carboxyl group, an ester group, a substituted orunsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1to C20 alkoxy group, a substituted or unsubstituted C6 to C30 arylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 heteroaryl group, and asubstituted or unsubstituted C2 to C20 heterocycloalkyl group, w and w′are independently an integer that is inclusively between 0 to 4, and r,s, r′, and s′ are independently an integer that is inclusively between 0to 5.

As described above, the squarylium compound has improved selective lightabsorbance in an infrared/near infrared wavelength spectrum of light andthus may be applied to an infrared cut film.

Hereinafter, an infrared cut film including the squarylium compoundrepresented by Chemical Formula 1 is described.

The infrared cut film may be manufactured by coating a compositionincluding the squarylium compound represented by Chemical Formula 1 andan organic solvent on a transparent substrate and removing the organicsolvent to manufacture a film.

The organic solvent may include for example ethers such asdimethoxyethane, methoxyethoxyethane, tetrahydrofuran, dioxane, and thelike, ketones such as acetone, methylethylketone, methylisobutylketone,cyclohexanone, and the like, aromatic hydrocarbons such as benzene,toluene, xylene, monochlorobenzene, and the like, which may be used inan amount of about 10 parts by weight to about 3000 parts by weightbased on 1 part by weight of the squarylium compound represented byChemical Formula 1.

The composition may further include a binder, and the binder may be forexample a polyester-based resin, a polycarbonate-based resin, apolyacrylic acid-based resin, a polystyrene-based resin, a polyvinylchloride-based resin, a polyvinyl acetate-based resin, and the like. Thebinder may be used in an amount of about 10 parts by weight to about 500parts by weight based on 1 part by weight of the squarylium compoundrepresented by Chemical Formula 1.

The composition including the squarylium compound represented byChemical Formula 1 may be coated on the transparent substrate using aknown method such as a bar coat method, a spray method, a roll coatingmethod, a dipping method, and the like.

In addition, the infrared cut film may be manufactured by dispersing thesquarylium compound represented by Chemical Formula 1 in a resin,molding the resultant, and making it into a film. The resin may beselected from a polyester-based resin, a polycarbonate-based resin, apolyacrylic acid-based resin, a polystyrene-based resin, a polyvinylchloride-based resin, and a polyvinyl acetate-based resin.

The infrared cut film may be manufactured by further adhering atransparent substrate to a surface of a base film that is manufacturedas above, as needed. The transparent substrate is not particularly aslong as it is transparent resin or glass having low absorption andscattering properties. The resin may be for example a polyester-basedresin, a polycarbonate-based resin, a polyacrylic acid-based resin, apolystyrene-based resin, a polyvinyl chloride-based resin, a polyvinylacetate-based resin, and the like.

The infrared cut film may be used as an infrared cut filter due toinfrared ray/near infrared ray cutting performance.

The infrared cut filter may include an infrared cut film including thesquarylium compound represented by Chemical Formula 1 and an infraredlight reflection layer disposed on the infrared cut film as needed. Aninfrared cut filter having such a structure is described referring toFIGS. 1 and 2.

In the drawings, the thickness of layers, films, panels, regions, etc.,are exaggerated for clarity. Like reference numerals designate likeelements throughout the disclosure. It will be understood that when anelement such as a layer, film, region, or substrate is referred to asbeing “on” another element, it can be directly on the other element orintervening elements may also be present. In contrast, when an elementis referred to as being “directly on” another element, there are nointervening elements present.

FIG. 1 is a schematic cross-sectional view of an infrared cut filteraccording to some example embodiments.

Referring to FIG. 1, an infrared cut filter 1 according to some exampleembodiments includes an infrared cut film 11 including the squaryliumcompound represented by Chemical Formula 1 and an infrared lightreflection layer 13 disposed on the infrared cut film 11.

The infrared cut film 11 may be manufactured by dispersing thesquarylium compound represented by Chemical Formula 1 in a resin,molding the resultant, and making it into a film as described above. Theinfrared cut film 11 may be a glass substrate including the squaryliumcompound represented by Chemical Formula 1. The glass substrate mayfurther include copper oxide.

The infrared light reflection layer 13 may be a thin film including aninorganic particulate and may be a deposition film of an inorganicparticulate or a metal deposition film. The inorganic particulate may beat least one particulate of silica (SiO₂), titania (TiO₂) alumina(Al₂O₃), zirconia, tantalum pentoxide, niobium pentoxide, lanthanumoxide, yttrium oxide, zinc oxide, zinc sulfide, indium oxide, tin oxide,lanthanum fluoride, magnesium fluoride, sodium hexafluoroaluminate, andthe like. Examples of the metal deposition film may be an aluminumdeposition film. The deposition film may be for example formed bydepositing an inorganic particulate or a metal using a CVD method, asputtering method, a vacuum deposition method, an ion-assist depositionmethod, an ion plating method, and the like on the infrared cut film 11,but is not limited thereto.

The infrared light reflection layer 13 may be a thin film that may beformed based on codepositing different kinds of inorganic particulatesor a multi-layered thin film including deposited different kinds ofinorganic particulates. For example, a first deposition film of aninorganic particulate that is at least one particulate of titania(TiO₂), zirconia, and a combination thereof is formed on the infraredcut film 11 and a second deposition film of an inorganic particulateselected from silica (SiO₂), alumina, and a combination thereof may beformed thereon. Such inorganic particulate deposition films of theinfrared light reflection layer 13 may include 5 to 30 repeated layers.

A thickness of the infrared cut film 11 may be about 50 μm to about 200μm, for example about 55 μm to about 190 μm or about 60 μm to about 180μm and a thickness of the infrared light reflection layer 13 may beabout 0.1 μm to about 20 μm, for example about 0.5 μm to about 10 μm, orabout 0.7 μm to about 5 μm. Within the ranges, infrared light cuttingperformance may be improved and mechanical strength may also be ensured.

FIG. 2 is a schematic cross-sectional view of an infrared cut filteraccording to some example embodiments.

Referring to FIG. 2, an infrared cut filter 2 according to some exampleembodiments includes an infrared cut film 21 including the squaryliumcompound represented by Chemical Formula 1 and a first infrared lightreflection layer 23 and a second infrared light reflection layer 25disposed on both surfaces of the infrared cut film 21.

The infrared cut film 21 may be manufactured by dispersing thesquarylium compound represented by Chemical Formula 1 in a resin,molding the resultant, and making it into a film as described above. Theinfrared cut film 21 may be a glass substrate including the squaryliumcompound represented by Chemical Formula 1. The glass substrate mayfurther include copper oxide.

The first infrared light reflection layer 23 and the second infraredlight reflection layer 25 may be a thin film including an inorganicparticulate and may be a deposition film of an inorganic particulate ora metal deposition film. The inorganic particulate may be silica (SiO₂),titania (TiO₂) alumina (Al₂O₃), zirconia, tantalum pentoxide, niobiumpentoxide, lanthanum oxide, yttrium oxide, zinc oxide, zinc sulfide,indium oxide, tin oxide, lanthanum fluoride, magnesium fluoride, sodiumhexafluoroaluminate, and the like. Examples of the metal deposition filmmay be an aluminum deposition film. The deposition film may be forexample formed by depositing an inorganic particulate or a metal using aCVD method, a sputtering method, a vacuum deposition method, anion-assist deposition method, an ion plating method, and the like on theinfrared cut film 21, but is not limited thereto.

The first infrared light reflection layer 23 and the second infraredlight reflection layer 25 reflect light in an infrared ray wavelengthspectrum of light effectively, and thereby optical distortion by lightin an infrared ray wavelength spectrum of light may be effectivelyreduced or prevented. The first infrared light reflection layer 23 andthe second infrared light reflection layer 25 may reflect light in apart of a near infrared wavelength spectrum of light, a mid-infraredwavelength spectrum of light, and a far-infrared wavelength spectrum oflight, for example light in a wavelength spectrum of light of about 700nm to 3 μm.

The first infrared light reflection layer 23 and the second infraredlight reflection layer 25 is not particularly limited as long as itreflects light in an infrared ray wavelength spectrum of light, and maybe for example a high refractive reflective layer, a reflective layerincluding a nano particle having a high refractive index or a multilayerincluding a plurality of layers having different refractive indexes, butis not limited thereto.

The first infrared light reflection layer 23 and the second infraredlight reflection layer 25 may be a thin film obtained by codepositingdifferent kinds of inorganic particulates or a multi-layered thin filmobtained by depositing different kinds of inorganic particulates.

For example, the first infrared light reflection layer 23 and the secondinfrared light reflection layer 25 may include a first layer and asecond layer consisting of each material having a different refractiveindex and may include a multilayer including the first layer and thesecond layer that are alternately and repeatedly stacked.

Each of the first layer and the second layer may be for example adielectric layer including oxide layer, a nitride layer, an oxynitridelayer, a sulfide layer, or a combination thereof, and for example thefirst layer may have a refractive index of less than about 1.7 and thesecond layer may have a refractive index of greater than or equal toabout 1.7. Within the ranges, for example the first layer may have arefractive index of greater than or equal to about 1.1 and less than 1.7and the second layer may have a refractive index of about 1.7 to about2.7, or within the ranges, for example the first layer may have arefractive index of about 1.2 to about 1.6 and the second layer may havea refractive index of about 1.8 to about 2.5.

The first layer and the second layer may include a material having therefractive indexes without a particular limit, and the first layer mayinclude for example silicon oxide, aluminum oxide, or a combinationthereof and the second layer may include titanium oxide, zinc oxide,indium oxide, zirconium oxide, or a combination thereof. The first layerand the second layer may have for example five layers to eighty layers,for example five layers to fifty layers.

Each thickness of the first layer and the second layer may be determinedaccording to a refractive index and a reflection wavelength of eachlayer and for example each first layer may have a thickness of about 10nm to about 700 nm and each second layer may have a thickness of about30 nm to about 600 nm. Thicknesses of the first layer and the secondlayer may be the same or different.

A thickness of the infrared cut film 21 may be about 50 μm to about 200μm, for example about 55 μm to about 190 μm or about 60 μm to about 180μm and each thickness of the first infrared light reflection layer 23and the second infrared light reflection layer 25 may be about 0.1 μm toabout 20 μm, for example about 0.5 μm to about 10 μm, or about 0.7 μm toabout 5 μm. Within the ranges, infrared light cutting performance may beimproved and mechanical strength may also be ensured.

As described above, the squarylium compound may be applied to variouselectronic devices due to improved selective light absorbance in aninfrared/near infrared wavelength spectrum of light. The electronicdevices may be for example an image sensor, a liquid crystal display, aplasma display, an organic electroluminescence display, a laser display,a solar cell, a bio sensor, an illumination, and the like. Particularly,a compound having improved absorbance in an infrared/near infraredwavelength spectrum of light such as the squarylium compound may improvespectral sensitivity at a low illumination, and may be usefully used inan iris identification sensor, a night vision device, and the like.

Hereinafter, an image sensor as an example of an electronic device iddescribed with reference to the drawings.

An image sensor according to some example embodiments includes a firstphoto-sensing device configured to sense light in a blue wavelengthspectrum of light,

a second photo-sensing device configured to sense light in a redwavelength spectrum of light,

a third photo-sensing device configured to sense light in a greenwavelength spectrum of light, and

a fourth photo-sensing device configured to sense light in aninfrared/near infrared wavelength spectrum of light,

wherein the fourth photo-sensing device may include the squaryliumcompound.

The first photo-sensing device to the fourth photo-sensing device may bearranged (may extend) adjacently and parallel or perpendicular, to eachother collectively in the form of a single group.

The first photo-sensing device to the fourth photo-sensing device mayeach be an inorganic photodiode or an organic photodiode and at leastone of the first photo-sensing device to the fourth photo-sensing devicemay be an organic photodiode.

The inorganic photodiode may be for example a silicon photodiode, but isnot limited thereto.

The organic photodiode may be an organic photoelectric device includinga pair of light-transmitting electrodes facing each other and aphotoactive layer disposed between them and including an organiclight-absorbing material.

One of the pair of light-transmitting electrodes may be an anode and theother may be a cathode. The light-transmitting electrodes may be madeof, for example, a transparent conductor such as indium tin oxide (ITO),indium zinc oxide (IZO), zinc oxide (ZnO), tin oxide (SnO), aluminum tinoxide (AlTO), and fluorine-doped tin oxide (FTO), or may be a metal thinlayer having a thin thickness of several nanometers or several tens ofnanometers or a metal thin layer having a thin thickness of severalnanometers to several tens of nanometers doped with a metal oxide.

The photoactive layer is a layer including a p-type semiconductormaterial and an n-type semiconductor material to provide a pn junction,which is a layer producing excitons by receiving light from outside andthen separating holes and electrons from the produced excitons.

The photoactive layer may include an intrinsic layer including both thep-type semiconductor and the n-type semiconductor and may be formedaccording to a method of, for example, co-deposition and the like. Inaddition, the photoactive layer may further include at least oneselected from a p-type layer and an n-type layer besides the intrinsiclayer, wherein the p-type layer may include a p-type semiconductormaterial, and the n-type layer may include an n-type semiconductormaterial. The kind of the p-type semiconductor material and the n-typesemiconductor material may be determined according to the absorptionwavelength.

At least one of charge auxiliary layers may be further included betweenthe light-transmitting electrode and the photoactive layer. The chargeauxiliary layer may further facilitate the movement of holes andelectrons separated from the photoactive layer to enhance efficiency,and may be at least one selected from, for example, a hole injectionlayer (HIL) facilitating hole injection, a hole transport layer (HTL)facilitating hole transportation, an electron blocking layer (EBL)blocking electron transportation, an electron injection layer (EIL)facilitating electron injection, an electron transport layer (ETL)facilitating electron transportation, and a hole blocking layer (HBL)blocking hole transportation.

The hole transport layer (HTL) may include, for example one selectedfrom poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate)(PEDOT:PSS), polyarylamine, poly(N-vinylcarbazole), polyaniline,polypyrrole, N,N,N′,N′-tetrakis(4-methoxyphenyl)-benzidine (TPD),4-bis[N-(1-naphthyl)-N-phenyl-amino]biphenyl (α-NPD), m-MTDATA,4,4′,4″-tris(N-carbazolyl)-triphenylamine (TCTA), tungsten oxide (WOx,0<x≤3), molybdenum oxide (MO_(x), 1<x≤3), vanadium oxide (V₂O₅), rheniumoxide, nickel oxide (NiO_(x), 1<x≤4), copper oxide, titanium oxide,molybdenum sulfide, and a combination thereof, but is not limitedthereto.

The electron blocking layer (EBL) may include one selected from, forexample, poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate)(PEDOT:PSS), polyarylamine, poly(N-vinylcarbazole), polyaniline,polypyrrole, N,N,N′,N′-tetrakis(4-methoxyphenyl)-benzidine (TPD),4-bis[N-(1-naphthyl)-N-phenyl-amino]biphenyl (α-NPD), m-MTDATA,4,4′,4″-tris(N-carbazolyl)-triphenylamine (TCTA), and a combinationthereof, but is not limited thereto.

The electron transport layer (ETL) may include one selected from, forexample, 1,4,5,8-naphthalene-tetracarboxylic dianhydride (NTCDA),bathocuproine (BCP), LiF, Alq3, Gaq3, Inq3, Znq2, Zn(BTZ)2, BeBq2,aluminum (Al), magnesium (Mg), molybdenum (Mo), aluminum oxide,magnesium oxide, molybdenum oxide, and a combination thereof, but is notlimited thereto.

The hole blocking layer (HBL) may include one selected from, for example1,4,5,8-naphthalene-tetracarboxylic dianhydride (NTCDA),dicyanovinyl-terthiophene (DCV3T), bathocuproine (BCP), LiF, Alq3, Gaq3,Inq3, Znq2, Zn(BTZ)2, BeBq2, and a combination thereof, but is notlimited thereto.

The organic photoelectric device may produce excitons at the insidethereof when light in a predetermined region is adsorbed in thephotoactive layer by entering light from one light-transmittingelectrode side. The excitons are separated into holes and electrons inthe photoactive layer, and the separated holes may be transported intoan anode side and the separated electrons may be transported into acathode side to flow current through the organic photoelectric device.

In an image sensor according to some example embodiments, the firstphoto-sensing device, the second photo-sensing device, the thirdphoto-sensing device, and the fourth photo-sensing device may be aninorganic photodiode.

FIG. 3 is a schematic cross-sectional view of an image sensor accordingto some example embodiments.

Referring to FIG. 3, an image sensor 100 includes a semiconductorsubstrate 110 integrated with a blue photodiode 50B, a green photodiode50G, a red photodiode 50R, an infrared light/near infrared light diode(infrared photodiode) 50IR, and a transmission transistor (not shown), alower insulation layer 65, a color filter layer 70, an upper insulationlayer 85, and an infrared cut filter 70IR.

The semiconductor substrate 110 may be a silicon substrate and may beintegrated with the blue photodiode 50B, the green photodiode 50G, thered photodiode 50R, the infrared light/near infrared light diode 50IR,and the transmission transistor (not shown). The blue photodiode 50B,the green photodiode 50G, the red photodiode 50R may be respectivelyintegrated in each of a blue pixel, a green pixel, and a red pixel. Theblue photodiode 50B, the green photodiode 50G, the red photodiode 50R,and the infrared light/near infrared light diode 50IR may sense light,and the sensed information may be transferred by a transport transistor.The transmission transistor may transfer photocharges generated by thephotodiode to a driving transistor (not shown).

Metal wires (not shown) and pads (not shown) are formed on thesemiconductor substrate 110. In order to decrease signal delay, themetal wires and pads may be made of a metal having low resistivity, forexample, aluminum (Al), copper (Cu), silver (Ag), and alloys thereof,but are not limited thereto.

The lower insulation layer 65 may be formed on the metal wires and pads.The lower insulation layer 65 may be made of an inorganic insulationmaterial such as a silicon oxide and/or a silicon nitride, or a lowdielectric constant (low K) material such as SiC, SiCOH, SiCO, and SiOF.

The color filter layer 70 formed on the lower insulation layer 65includes a blue filter 70B formed in a blue pixel, a green filter 70Gformed in a green pixel, and a red filter 70R formed in a red pixel.

The upper insulation layer 85 is formed on the color filter layer 70.The upper insulation layer 85 removes steps caused by the color filterlayer 70, and planarize it. The upper insulation layer 85 and the lowerinsulation layer 65 may include a contact hole (not shown) to exposepads.

The infrared cut filter 70IR is formed on the upper insulation layer 85.The infrared cut filter 70IR includes the squarylium compoundrepresented by Chemical Formula 1. The infrared cut film (IR) mayselectively absorb light in an infrared ray (particularly, near infraredray) region of greater than or equal to about 700 nm and less than orequal to about 1300 nm without absorption in a visible wavelengthspectrum of light.

As described above, the color filter layer 70 including the colorfilters 70B, 70G, and 70R absorbing light in a visible ray region andthe infrared cut filter 70IR are vertically stacked and thereby an areaabsorbing infrared light may be enlarged and absorption efficiency maybe increased.

A focusing lens (not shown) may be further formed on the infrared cutfilter 70IR. The focusing lens may control a direction of incident lightand gather the light in one region. The focusing lens may have a shapeof, for example, a cylinder or a hemisphere, but is not limited thereto.

As shown in FIG. 4, an image sensor 200 includes a focusing lens 90formed on the upper insulation layer 85 and the infrared cut filter 70IRformed on the focusing lens 90.

In an image sensor according to some example embodiments, the infraredcut filter 70IR may be disposed only on an infrared light/near infraredlight diode. FIG. 5 is a schematic cross-sectional view showing such animage sensor 30.

In an image sensor according to some example embodiments, the firstphoto-sensing device (“photodiode”), the second photo-sensing device,and the third photo-sensing device may be an organic photodiode and thefourth photo-sensing device may be an inorganic photodiode.

FIG. 6 is a schematic cross-sectional view showing an image sensoraccording to some example embodiments.

Referring to FIG. 6, an image sensor 400 according to some exampleembodiments includes a semiconductor substrate 110 integrated with aninfrared photodiode 50IR, a blue charge storage 55B, a green chargestorage 55G, a red charge storage 55R, and a transmission transistor(not shown), a lower insulation layer 65, an upper insulation layer 85,a blue photo-sensing device 100B, a green photo-sensing device 100G, anda red photo-sensing device 100R.

The semiconductor substrate 110 may be a silicon substrate, and may beintegrated with the infrared photodiode 50IR, the blue charge storage55B, the green charge storage 55G, the red charge storage 55R, and thetransmission transistor (not shown). The blue charge storage 55B, thegreen charge storage 55G, and the red charge storage 55R may berespectively integrated in each of a blue pixel, a green pixel, and ared pixel. The infrared photodiode 50IR may absorb light in an infraredray (particularly, a near infrared ray) region and the sensedinformation may be transferred by a transport transistor.

Charges absorbed in the blue photo-sensing device 100B, the greenphoto-sensing device 100G, and the red photo-sensing device 100R arecollected in the blue charge storage 55B, the green charge storage 55G,and the red charge storage 55R which are electrically connected to eachof the blue photo-sensing device 100B, the green photo-sensing device100G, and the red photo-sensing device 100R.

Metal wires (not shown) and pads (not shown) are formed on thesemiconductor substrate 110. In order to decrease signal delay, themetal wires and pads may be made of a metal having low resistivity, forexample, aluminum (Al), copper (Cu), silver (Ag), and alloys thereof,but are not limited thereto.

The lower insulation layer 65 may be formed on the metal wires and pads.The lower insulation layer 65 may be made of an inorganic insulationmaterial such as a silicon oxide and/or a silicon nitride, or a lowdielectric constant (low K) material such as SiC, SiCOH, SiCO, and SiOF.

The blue photo-sensing device 100B, the green photo-sensing device 100G,and the red photo-sensing device 100R are formed on the lower insulationlayer 65. The blue photo-sensing device 100B includes a lower electrode10B, an upper electrode 20B, and a photoactive layer 30B selectivelyabsorbing light in a blue wavelength spectrum of light, the greenphoto-sensing device 100G includes a lower electrode 10G, an upperelectrode 20G and a photoactive layer 30G selectively absorbing light ina green wavelength spectrum of light, and the red photo-sensing device100R includes a lower electrode 10R, an upper electrode 20R, and aphotoactive layer 30R selectively absorbing light in a red wavelengthspectrum of light.

The lower electrodes 10B, 10G, and 10R and the upper electrodes 20B,20G, and 20R may be light-transmitting electrodes and may be made of,for example, a transparent conductor such as indium tin oxide (ITO),indium zinc oxide (IZO), zinc oxide (ZnO), tin oxide (SnO), aluminum tinoxide (AlTO), and fluorine-doped tin oxide (FTO), or may be a metal thinlayer having a thin thickness of several nanometers or several tens ofnanometers or a metal thin layer having a thin thickness of severalnanometers to several tens of nanometers doped with a metal oxide.

The photoactive layers 30B, 30G, and 30R may include a p-typesemiconductor material and an n-type semiconductor material. Thephotoactive layer 30B of the blue photo-sensing device 100B may includea p-type semiconductor material selectively absorbing light in a bluewavelength spectrum of light and an n-type semiconductor materialselectively absorbing light in a blue wavelength spectrum of light, thephotoactive layer 30G of the green photo-sensing device 100G may includea p-type semiconductor material selectively absorbing light in a greenwavelength spectrum of light and an n-type semiconductor materialselectively absorbing light in a green wavelength spectrum of light, andthe photoactive layer 30R of the red photo-sensing device 100R mayinclude a p-type semiconductor material selectively absorbing light in ared wavelength spectrum of light and an n-type semiconductor materialselectively absorbing light in a red wavelength spectrum of light.

The upper insulation layer 85 is formed on the lower insulation layer65. The upper insulation layer 85 is disposed on the infrared photodiode50IR and may reduce steps with the blue photo-sensing device 100B, thegreen photo-sensing device 100G, and the red photo-sensing device 100R.

The infrared cut filter 70IR is disposed on the blue photo-sensingdevice 100B, the green photo-sensing device 100G, the red photo-sensingdevice 100R, and the upper insulation layer 85. The infrared cut filter70IR includes the squarylium compound represented by Chemical Formula 1.The infrared cut film (IR) may selectively absorb light in an infraredray (particularly, near infrared ray) region of greater than or equal toabout 700 nm and less than or equal to about 1300 nm without absorptionin a visible wavelength spectrum of light.

As shown in FIG. 6, the infrared cut filter 70IR is formed on an entiresurface of a blue pixel, a green pixel, and a red pixel, and thereby anarea absorbing infrared light may be enlarged and absorption efficiencymay be increased.

The blue photo-sensing device 100B, the green photo-sensing device 100G,and the red photo-sensing device 100R may be vertically stacked. In thisway, the area of the image sensor may be decreased and down-sizing ofthe image sensor may be implemented by stacking the photo-sensingdevices 100B, 100G, and 100R vertically. A stacking order of thephoto-sensing devices 100B, 100G, and 100R are not particularly limited.

A focusing lens (not shown) may be further formed on the infrared rayfilter 70IR. The focusing lens may control a direction of incident lightand gather the light in one region. The focusing lens may have a shapeof, for example, a cylinder or a hemisphere, but is not limited thereto.

In addition, the image sensor 400 may include a focusing lens formed onthe blue photo-sensing device 100B, the green photo-sensing device 100G,the red photo-sensing device 100R, and the upper insulation layer 85,and the infrared ray filter 70IR formed on the focusing lens.

The infrared ray filter 70IR of FIG. 6 may be formed at a positioncorresponding to the infrared light/near infrared light diode 50IR asshown in FIG. 5.

In an image sensor according to some example embodiments, the thirdphoto-sensing device may be an organic photodiode and the firstphoto-sensing device, the second photo-sensing device, and the fourthphoto-sensing device may be an inorganic photodiode.

FIG. 7 is a schematic cross-sectional view showing an image sensoraccording to some example embodiments.

Referring to FIG. 7, an image sensor 50 according to some exampleembodiments includes a semiconductor substrate 110 integrated with ablue photodiode 50B, a red photodiode 50R, a green charge storage 55G,an infrared light/near infrared light diode 50IR, and a transmissiontransistor (not shown), a lower insulation layer 65, color filter layers(“color filters”) 70B and 70R, a first upper insulation layer 85 a, agreen photo-sensing device 100G, a second upper insulation layer 85 b,and an infrared ray filter 70IR.

The semiconductor substrate 110 may be a silicon substrate and may beintegrated with the blue photodiode 50B, the red photodiode 50R, thegreen charge storage 55G, the infrared light/near infrared light diode50IR, and the transmission transistor (not shown). The blue photodiode50B and the transmission transistor may be integrated in each of a bluepixel, the red photodiode 50R and the transmission transistor integratedin each of a red pixel, and the green charge storage 55G and thetransmission transistor integrated in each of a green pixel.

Metal wires (not shown) and pads (not shown) are formed on thesemiconductor substrate 110. In order to decrease signal delay, themetal wires and pads may be made of a metal having low resistivity, forexample, aluminum (Al), copper (Cu), silver (Ag), and alloys thereof,but are not limited thereto. However, the image sensor is not limited tothe structure and the metal wires and pads may be disposed under theblue photodiode 50B, the red photodiode 50R, the green charge storage55G, and the infrared light/near infrared light diode 50IR.

The lower insulation layer 65 may be formed on the metal wires and pads.The lower insulation layer 65 may be made of an inorganic insulationmaterial such as a silicon oxide and/or a silicon nitride, or a lowdielectric constant (low K) material such as SiC, SiCOH, SiCO, and SiOF.

Color filters 70B and 70R may be formed on the lower insulation layer65. The color filter 70B of the blue pixel adsorbs light in the bluewavelength spectrum of light and transfers it to the blue photo-sensingdevice 50B, and the color filter 70R of the red pixel adsorbs light inthe red wavelength spectrum of light and transfers it to the redphoto-sensing device 50R. The green pixel does not include a colorfilter.

The first upper insulation layer 85 a is formed on the color filters 70Band 70R. The first upper insulation layer 85 a removes steps caused bythe color filter 70B and 70R, and planarizes it.

The green photo-sensing device 100G and the second upper insulationlayer 85 b are formed on the first upper insulation layer 85 a. Thegreen photo-sensing device 100G includes light-transmitting electrodes10G and 20G and a photoactive layer 30G.

One of the light-transmitting electrodes 10G and 20G may be an anode andthe other may be a cathode. The light-transmitting electrodes 10G and20G may be made of, for example, a transparent conductor such as indiumtin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), tin oxide(SnO), aluminum tin oxide (AlTO), and fluorine-doped tin oxide (FTO), ormay be a metal thin layer having a thin thickness of several nanometersor several tens of nanometers or a metal thin layer having a thinthickness of several nanometers to several tens of nanometers doped witha metal oxide.

The photoactive layer 30G selectively absorbs light in a greenwavelength spectrum of light and passes light in other wavelengthspectrum of lights except the green wavelength spectrum of light, whichare the blue wavelength spectrum of light and the red wavelengthspectrum of light.

The photoactive layer 30G may include a p-type semiconductor compoundselectively adsorbing light in the green wavelength spectrum of lightand an n-type semiconductor compound selectively adsorbing light in thegreen wavelength spectrum of light, and the p-type semiconductorcompound and the n-type semiconductor compound may provide a pnjunction. The photoactive layer 30G selectively adsorbs light in thegreen wavelength spectrum of light and produces excitons, and then theproduced excitons are separated into holes and electrons to impart thephotoelectric effects. The photoactive layer 30G may be substituted fora color filter of the green pixel.

Each of the p-type semiconductor material and the n-type semiconductormaterial may have an energy bandgap of, for example, about 2.0 to about2.5 eV, and the p-type semiconductor material and the n-typesemiconductor material may have a LUMO difference of, for example, about0.2 to about 0.7 eV.

The p-type semiconductor material may be, for example, quinacridone or aderivative thereof, and the n-type semiconductor material may be, forexample, a cyanovinyl group-containing a thiophene derivative, but theyare not limited thereto.

The green photo-sensing device 100G may produce excitons at the insidewhen light enters from the upper electrode 20G, and the photoactivelayer 30G absorbs light in the green wavelength spectrum of light.Excitons are separated into holes and electrons in the photoactive layer30G, and the separated holes are moved to the anode side, which is oneof the lower electrode 10G and the upper electrode 20G, and theseparated electrons are moved to a cathode which is the other of thelower electrode 10G and the upper electrode 20G, so as to flow acurrent. The separated electrons or holes may be collected in the chargestorage 55G. Light in other wavelength spectrum of lights except thegreen wavelength spectrum of light may pass through the greenphoto-sensing device 100G and the color filters 70B and 70R, and may besensed by the blue photo-sensing device 50B or the red photo-sensingdevice 50R.

The photoactive layer 30G may be formed on an entire surface of the bluepixel (B), the red pixel (R), and the green pixel (G), such that thelight absorption area is increased to accomplish the highlight-absorptive efficiency.

The second upper insulation layer 85 b may be disposed on the infraredphotodiode 50IR and may reduce steps with the green photo-sensing device100G.

The infrared cut filter 70IR is formed on the green photo-sensing device100G and the upper insulation layer 80 b. The infrared cut filter 70IRincludes the squarylium compound represented by Chemical Formula 1. Theinfrared cut film (IR) may selectively absorb light in an infrared ray(particularly, near infrared ray) region of greater than or equal toabout 700 nm and less than or equal to about 1300 nm without absorptionin a visible wavelength spectrum of light.

A focusing lens (not shown) may be further formed on the infrared rayfilter 70IR. The focusing lens may control a direction of incident lightand gather the light in one region. The focusing lens may have a shapeof, for example, a cylinder or a hemisphere, but is not limited thereto.

In addition, the image sensor 50 may include a focusing lens formed onthe green photo-sensing device 100G and the second upper insulationlayer 85 b and the infrared cut filter 70IR formed on the focusing lens.

In some example embodiments, for better understanding and ease ofdescription, the structure in which the green photo-sensing device 100Gis stacked is exemplified, but it is not limited thereto. The structuremay be stacked with the red photo-sensing device 100R or the bluephoto-sensing device 100B instead of the green photo-sensing device100G.

As described above, an area of the image sensor may be decreased anddown-sizing of the image sensor may be implemented by verticallystacking a color filter layer including color filters absorbing light ina blue wavelength spectrum of light and light in a red wavelengthspectrum of light of a visible ray region, a green photo-sensing deviceabsorbing light in a green wavelength spectrum of light, and an infraredcut filter absorbing light in an infrared light. In addition, aphoto-sensing device selectively absorbing light in a green wavelengthspectrum of light and an infrared cut filter are formed on an entiresurface of an image sensor and an area absorbing light may be enlargedand absorption efficiency may be increased.

In an image sensor according to some example embodiments, the firstphoto-sensing device, the second photo-sensing device, the thirdphoto-sensing device, and the fourth photo-sensing device may be anorganic photodiode.

FIG. 8 is a schematic cross-sectional view showing an image sensoraccording to some example embodiments.

Referring to FIG. 8, an image sensor 600 according to some exampleembodiments includes a semiconductor substrate 110 integrated with aninfrared light/near infrared light charge storage 55IR, a blue chargestorage 55B, a green charge storage 55G, a red charge storage 55R, and atransmission transistor (not shown), a lower insulation layer 65, a bluephoto-sensing device 100B, a green photo-sensing device 100G, a redphoto-sensing device 100R and an infrared/near infrared photo-sensingdevice 100IR.

The semiconductor substrate 110 may be a silicon substrate and may beintegrated with the infrared light/near infrared light charge storage55IR, the blue charge storage 55B, the green charge storage 55G, the redcharge storage 55R, and the transmission transistor (not shown). Theblue charge storage 55B, the green charge storage 55G, and the redcharge storage 55R may be respectively integrated in each of a bluepixel, a green pixel, and a red pixel.

Charges absorbed in the infrared/near infrared photo-sensing device100IR, the blue photo-sensing device 100B, the green photo-sensingdevice 100G, and the red photo-sensing device 100R are collected in inthe infrared light/near infrared light charge storage 55IR, the bluecharge storage 55B, the green charge storage 55G, and the red chargestorage 55R which are electrically connected to each of theinfrared/near infrared photo-sensing device 100IR, the bluephoto-sensing device 100B, the green photo-sensing device 100G, and thered photo-sensing device 100R.

Metal wires (not shown) and pads (not shown) are formed on thesemiconductor substrate 110. In order to decrease signal delay, themetal wires and pads may be made of a metal having low resistivity, forexample, aluminum (Al), copper (Cu), silver (Ag), and alloys thereof,but are not limited thereto.

The lower insulation layer 65 may be formed on the metal wires and pads.The lower insulation layer 65 may be made of an inorganic insulationmaterial such as a silicon oxide and/or a silicon nitride, or a lowdielectric constant (low K) material such as SiC, SiCOH, SiCO, and SiOF.

The blue photo-sensing device 100B, the green photo-sensing device 100G,the red photo-sensing device 100R, and the infrared/near infraredphoto-sensing device 100IR are formed on the lower insulation layer 65.The blue photo-sensing device 100B includes a lower electrode 10B, anupper electrode 20B, and a photoactive layer 30B selectively absorbinglight in a blue wavelength spectrum of light, the green photo-sensingdevice 100G includes a lower electrode 10G, an upper electrode 20G and aphotoactive layer 30G selectively absorbing light in a green wavelengthspectrum of light, the red photo-sensing device 100R includes a lowerelectrode 10R, an upper electrode 20R, and a photoactive layer 30Rselectively absorbing light in a red wavelength spectrum of light, andthe infrared/near infrared photo-sensing device 100IR includes a lowerelectrode 10IR, an upper electrode 20IR, and a photoactive layer 30IRselectively absorbing light in an infrared/near infrared wavelengthspectrum of light.

The lower electrodes 10B, 10G, 10R, and 10IR and the upper electrodes20B, 20G, 20R, and 20IR may be light-transmitting electrodes and may bemade of, for example, a transparent conductor such as indium tin oxide(ITO), indium zinc oxide (IZO), zinc oxide (ZnO), tin oxide (SnO),aluminum tin oxide (AlTO), and fluorine-doped tin oxide (FTO), or may bea metal thin layer having a thin thickness of several nanometers orseveral tens of nanometers or a metal thin layer having a thin thicknessof several nanometers to several tens of nanometers doped with a metaloxide.

The photoactive layers 30B, 30G, 30R, and 30IR may include a p-typesemiconductor material and an n-type semiconductor material. Thephotoactive layer 30B of the blue photo-sensing device 100B may includea p-type semiconductor material selectively absorbing light in a bluewavelength spectrum of light and an n-type semiconductor materialselectively absorbing light in a blue wavelength spectrum of light, thephotoactive layer 30G of the green photo-sensing device 100G may includea p-type semiconductor material selectively absorbing light in a greenwavelength spectrum of light and an n-type semiconductor materialselectively absorbing light in a green wavelength spectrum of light, thephotoactive layer 30R of the red photo-sensing device 100R may include ap-type semiconductor material selectively absorbing light in a redwavelength spectrum of light and an n-type semiconductor materialselectively absorbing light in a red wavelength spectrum of light, andthe photoactive layer 30IR of the infrared/near infrared photo-sensingdevice 100IR may include a p-type semiconductor material selectivelyabsorbing light in an infrared wavelength spectrum of light and ann-type semiconductor material selectively absorbing light in an infraredwavelength spectrum of light.

The photoactive layer 30IR of the infrared/near infrared photo-sensingdevice 100IR uses the squarylium compound represented by ChemicalFormula 1 as a p-type semiconductor material and sub-phthalocyanine or asub-phthalocyanine derivative, fullerene or a fullerene derivative,thiophene or a thiophene derivative, or a combination thereof as ann-type semiconductor material. The fullerene may include C60, C70, C76,C78, C80, C82, C84, C90, C96, C240, C540, a mixture thereof, a fullerenenanotube, and the like. The fullerene derivative may refer to compoundsof these fullerenes having a substituent attached thereto. The fullerenederivative may include a substituent such as alkyl group, aryl group, ora heterocyclic group. Examples of the aryl groups and heterocyclicgroups may be are a benzene ring, a naphthalene ring, an anthracenering, a phenanthrene ring, a fluorene ring, a triphenylene ring, anaphthacene ring, a biphenyl ring, a pyrrole ring, a furan ring, athiophene ring, an imidazole ring, an oxazole ring, a thiazole ring, apyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, anindolizine ring, an indole ring, a benzofuran ring, a benzothiophenering, an isobenzofuran ring, a benzimidazole ring, an imidazopyridinering, a quinolizidine ring, a quinoline ring, a phthalazine ring, anaphthyridine ring, a quinoxaline ring, a quinoxazoline ring, anisoquinoline ring, a carbazole ring, a phenanthridine ring, an acridinering, a phenanthroline ring, a thianthrene ring, a chromene ring, anxanthene ring, a phenoxathin ring, a phenothiazine ring, or a phenazinering.

The infrared/near infrared photo-sensing device 100IR may selectivelyabsorb light in an infrared ray (particularly, near infrared ray) regionof greater than or equal to about 700 nm and less than or equal to about1300 nm without absorption in a visible wavelength spectrum of light.

FIGS. 9 and 10 are schematic cross-sectional views of an image sensoraccording to some example embodiments.

Referring to FIG. 9, an image sensor 700 includes a semiconductorsubstrate 110 integrated with an infrared light/near infrared lightcharge storage 55IR, a blue charge storage 55B, a green charge storage55G, a red charge storage 55R, and a transmission transistor (notshown), a lower insulation layer 65, a blue photo-sensing device 100B, agreen photo-sensing device 100G, a red photo-sensing device 100R, and aninfrared/near infrared photo-sensing device 100IR. The infrared/nearinfrared photo-sensing device 100IR is formed on an entire surface ofthe blue photo-sensing device 100B, the green photo-sensing device 100G,and the red photo-sensing device 100R. Other structures are the same asthe image sensor of FIG. 8.

In the structure of FIG. 9, the infrared/near infrared photo-sensingdevice 100IR may be disposed on the lower insulation layer 65 and theblue photo-sensing device 100B, the green photo-sensing device 100G, andthe red photo-sensing device 100R may be disposed thereon. An imagesensor having such a structure is shown in FIG. 10.

The infrared/near infrared photo-sensing device 100IR may selectivelyabsorb light in an infrared ray (particularly, near infrared ray) regionof greater than or equal to about 700 nm and less than or equal to about1300 nm without absorption in a visible wavelength spectrum of light andmay improve efficiency due to a large absorption area.

FIG. 11 is a schematic cross-sectional view of an image sensor accordingto some example embodiments.

Referring to FIG. 11, an image sensor 900 includes a semiconductorsubstrate 110 integrated with a blue charge storage 55B, a green chargestorage 55G, a red charge storage 55R, and a transmission transistor(not shown); a lower insulation layer 65, a color filter layer (70) anda upper insulation layer 85 on the semiconductor substrate 110; and aninfrared/near infrared photo-sensing device 100IR under thesemiconductor substrate 110.

FIG. 12 is a schematic cross-sectional view of an image sensor accordingto some example embodiments.

Referring to FIG. 12, an image sensor 1000 includes a semiconductorsubstrate 110 integrated with a blue photodiode 50B, a red photodiode50R, a green photodiode 50G, an infrared light/near infrared lightcharge storage 55IR, and a transmission transistor (not shown); a lowerinsulation layer 65; a blue filter 70B; a green filter 70G; a red filter70R; a upper insulation layer 85 a; and an infrared/near infraredphoto-sensing device 100IR.

FIG. 13 is a schematic cross-sectional view of an image sensor accordingto some example embodiments.

Referring to FIG. 13, an image sensor 1100 includes a semiconductorsubstrate 110 integrated with an infrared light/near infrared lightcharge storage 55IR, a blue storage 55B, a green storage 55G, a redstorage 55R and a transmission transistor (not shown); a lowerinsulation layer 65; a blue photo-sensing device 100B, a greenphoto-sensing device 100G, a red photo-sensing device 100R, aninfrared/near infrared photo-sensing device 100IR, a blue filter 70B, agreen filter 70G, and a red filter 70R.

FIG. 14 is a schematic cross-sectional view of an image sensor accordingto some example embodiments.

Referring to FIG. 14, an image sensor 1200 includes a semiconductorsubstrate 110 integrated with an infrared light/near infrared lightcharge storage 55IR, a blue storage 55B, a green storage 55G, a redstorage 55R and a transmission transistor (not shown); a lowerinsulation layer 65; a blue photo-sensing device 100B, a greenphoto-sensing device 100G, a red photo-sensing device 100R, aninfrared/near infrared photo-sensing device 100IR, a blue filter 70B, agreen filter 70G, and a red filter 70R.

FIG. 15 is a schematic cross-sectional view of an image sensor accordingto some example embodiments.

Referring to FIG. 15, an image sensor 1300 includes a semiconductorsubstrate 110 integrated with an infrared light/near infrared lightcharge storage 55IR, a blue storage 55B, a green storage 55G, a redstorage 55R and a transmission transistor (not shown); a lowerinsulation layer 65; a blue filter 70B; a red filter 70R; a upperinsulation layers 85 a and 85 b; a green photo-sensing device 100G; andan infrared/near infrared photo-sensing device 100IR.

FIG. 16 is a schematic cross-sectional view of an image sensor accordingto some example embodiments.

In the image sensor 1400 of FIG. 16, the blue photodiode 50B and the redphotodiode 50R are stacked perpendicularly, differing from the imagesensor 1300 of FIG. 15.

FIG. 17 is a schematic cross-sectional view of an image sensor accordingto some example embodiments.

Referring to FIG. 17, an image sensor 1500 includes a semiconductorsubstrate 110 integrated with an infrared light/near infrared lightcharge storage 55IR, a blue storage 55B, a green storage 55G, a redstorage 55R and a transmission transistor (not shown); a lowerinsulation layer 65; a blue filter 70B; a red filter 70R; a upperinsulation layers 85 a and 85 b; an infrared/near infrared photo-sensingdevice 100IR; and a green photo-sensing device 100G.

FIG. 18 is a schematic cross-sectional view of an image sensor accordingto some example embodiments.

In the image sensor 1600 of FIG. 18, the blue photodiode 50B and the redphotodiode 50R are stacked perpendicularly, differing from the imagesensor 1500 of FIG. 17.

The image sensor may be applied to various electronic devices, forexample, a mobile phone, a digital camera, and the like but is notlimited thereto.

FIG. 19 is a block diagram of a digital camera including an image sensoraccording to some example embodiments.

Referring to FIG. 19, a digital camera 1900 includes a lens 1010, animage sensor 1020, a motor unit 1030, and an engine unit 1040. The imagesensor 1020 may be one of image sensors according to embodiments shownin FIGS. 2 to 18.

The lens 1010 concentrates incident light on the image sensor 1020. Theimage sensor 1020 generates RGB data for received light through the lens1010.

In some embodiments, the image sensor 1020 may interface with the engineunit 1040.

The motor unit 1030 may adjust the focus of the lens 1010 or performshuttering in response to a control signal received from the engine unit1040. The engine unit 1040 may control the image sensor 1020 and themotor unit 1030.

The engine unit 1040 may be connected to a host/application 1050.

Hereinafter, some example embodiments are illustrated in more detailwith reference to examples. However, it will be understood that theseare examples, and the present disclosure is not limited thereto.

Synthesis Example I Synthesis Example 1

2.86 g (20 mmol) of 2-methylquinoline (Compound (1)) and 2.66 g (24mmol) of selenium dioxide are added to 50 ml of dioxane and reacted at120° C. for 5 hours to obtain Compound (2). Non-reacted reactants arefiltered, 3.164 g (20 mmol) of 1,8-diaminonaphthalene and 0.5 ml ofacetic acid are added thereto, and further reaction is performed for 3hours to obtain a red powder. The powder is filtered and the resultantis washed with dioxane and acetone several times and purified with acolumn chromatography to obtain 99.5% of Compound (3).

1.16 g (5 mmol) of 3,4-dihydroxycyclobutane-1,2-dione (Compound (4)) and2.95 g (10 mmol) of Compound (3) are reacted in 40 ml of atoluene/butanol (a volume ratio of 1:1) solution at 140° C. for 12hours, and the obtained product is filtered and purified with a columnchromatography to obtain final Compound A with a purity of 99.8%.

Absorbance of Compound A of Synthesis Example 1 is measured and shown inFIG. 20.

FIG. 20 is a graph showing absorbance depending on a wavelength ofCompound A obtained in Synthesis Example 1.

Referring to FIG. 20, Compound A has a maximum absorption wavelength atabout 854 nm and high infrared light wavelength selectivity in about 850nm to about 900 nm.

Synthesis Examples 2 to 15

Compounds B to O are synthesized by the same method as Synthesis Example1 except for using each reactant of Table 1 instead of2-methylquinoline.

TABLE 1 Syn- thesis Exam- Com- ple pound Reactant Final compounds 1 A

2 B

3 C

4 D

5 E

6 F

7 G

8 H

9 I

10 J

11 K

12 L

13 M

14 N

15 O

Evaluation I

Maximum absorption wavelengths (λ_(max)) and extinction coefficients ofCompounds A to O of Synthesis Examples 1 to 15 are measured. The maximumabsorption wavelengths (λ_(max)) and absorbances are measured bydissolving each compound in dichloromethane to prepare a solution andmeasuring with a UV-Vis spectrometer.

The results are shown in Table 2.

TABLE 2 Synthesis Examples Compounds λ_(max) (nm) A_(NIR)/A_(VIS) 1 A854 22.22 2 B 757 16.03 3 C 768 38.46 4 D 757 17.86 5 E 758 526.31 6 F781 28.57 7 G 914 21.74 8 H 778 11.36 9 I 807 12.35 10 J 715 43.48 11 K720 17.54 12 L 726 9.09 13 M 715 41.67 14 N 763 73.72 15 O 712 62.5 *A_(NIR): maximum absorption coefficient in an infrared ray (IR) region *A_(VIS): maximum absorption coefficient in a visible wavelength spectrumof light

Referring to Table 2, compounds of Synthesis Examples 1 to 15 have amaximum absorption wavelength of greater than or equal to 700 nm andA_(NIR)/A_(VIS) of greater than or equal to 8 which indicates highinfrared light absorption selectivity.

Synthesis Example II Synthesis Example 16

3,4-diisopropoxycyclobut-3-2n2-1,2-dione (Compound (1)) is reacted withdiphenylamine in a solution including thick hydrochloric acid inpropylalcohol and the resultant refluxed for 3 hours to obtain Compound(2). Compound (5) is synthesized in the same process as in ReactionScheme A except for using 2-methylpyridine (Compound (3)) instead of2-methylquinoline. Subsequently, 1.33 g (5 mmol) of3-(diphenylamino)-4-hydroxycyclobut-3-ene-1,2-dione and 1.23 g (5 mmol)of Compound (5) (2-(pyridine-2-yl)-1H-perimidine) are reacted in 40 mlof toluene/butanol (a volume ratio of 1:1) solvent at 140° C. for 12hours, and the obtained product is filtered and purified with columnchromatography to obtain a final compound, Compound Q with a purity of99.7%.

Absorbance of the obtained Compound Q is measured and shown in FIG. 21.

FIG. 21 is a graph showing absorbance depending on a wavelength ofCompound Q obtained in Synthesis Example 16.

Referring to FIG. 21, Compound Q has (“is configured to have”) a maximumabsorption wavelength at about 800 nm and high infrared light wavelengthselectivity in about 750 nm to 850 nm.

Synthesis Example 17

Compound (1) (4′-bromo-3,5-dimethoxy-1,1′-bipheny) and diphenylamine arereacted in 50 ml of toluene in the presence of a catalyst Pd₂(dba)₃ andt-BuONa at 120° C. for 8 hours to obtain Compound (2), and obtainedCompound (2) is reacted with BBr₃ under CH₂Cl₂ to obtain Compound (3).Subsequently, 3.53 g (10 mmol) of Compound (3) and 580.35 mg (5 mmol) ofCompound (4) are reacted in 40 ml of a toluene/butanol (a volume ratioof 1:1) solvent for 140° C. for 12 hours, and the obtained product isfiltered and purified with a column chromatography to obtain a finalcompound, Compound R with a purity of 99.7%.

Absorbance of Compound R is measured and shown in FIG. 22.

FIG. 22 is a graph showing absorbance depending on a wavelength ofCompound R obtained in Synthesis Example 17.

Referring to FIG. 22, Compound R has a maximum absorption wavelength atabout 800 nm and high infrared light wavelength selectivity in about 750nm to 850 nm.

Comparative Synthesis Example 1

Compound (1) (1-bromo-3,5-dimethoxybenzene) and diphenylamine arereacted in 50 ml of toluene in the presence of a catalyst, Pd₂(dba)₃ andt-BuONa at 120° C. for 8 hours to obtain Compound (2), and obtainedCompound (2) is reacted with BBr₃ under CH₂Cl₂ to obtain Compound (3).Subsequently, 2.77 g (10 mmol) of Compound (3) and 580.35 mg (5 mmol) ofCompound (4) are reacted in 40 ml of toluene/butanol (a volume ratio of1:1) solvent for 140° C. for 12 hours, and the obtained product isfiltered and purified with a column chromatography to obtain a finalcompound, Compound T with a purity of 99.7%.

Absorbance of the compound T obtained in Comparative Synthesis Example 1is measured and shown in FIG. 23.

FIG. 23 is a graph showing absorbance depending on a wavelength ofCompound T obtained in Comparative Synthesis Example 1.

Referring to FIG. 23, Compound T has a maximum absorption wavelength atabout 650 nm and shows main absorption in a visible ray region.

Comparative Synthesis Example 2

Absorbance of Compound U is measured and shown in FIG. 24.

FIG. 24 is a graph showing absorbance depending on a wavelength ofCompound U obtained in Comparative Synthesis Example 2.

Referring to FIG. 24, Compound U shows light absorption characteristicsin a broad range of about 650 nm to 840 nm.

Comparative Synthesis Example 3

Absorbance of Compound V disclosed in US 2008-0230123 A1 is shown inFIG. 25.

FIG. 25 is a graph showing absorbance depending on a wavelength ofCompound V obtained in Comparative Synthesis Example 3.

Referring to FIG. 25, Compound V shows light absorption characteristicsin broad ranges of about 300 nm to 450 nm and about 550 nm to 800 nm andlow A_(NIR)/A_(VIS) ratio of 0.65.

Comparative Synthesis Example 4

Absorbance of Compound W disclosed in US 2008-0230123 A1 is shown inFIG. 26.

FIG. 26 is a graph showing absorbance depending on a wavelength ofCompound W obtained in Comparative Synthesis Example 4.

Referring to FIG. 26, Compound W shows light absorption characteristicsin broad ranges of about 300 nm to 450 nm and about 650 nm to 800 nm andlow A_(NIR)/A_(VIS) ratio.

While this disclosure has been described in connection with what ispresently considered to be practical example embodiments, it is to beunderstood that the inventive concepts are not limited to the disclosedembodiments, but, on the contrary, is intended to cover variousmodifications and equivalent arrangements included within the spirit andscope of the appended claims.

What is claimed is:
 1. A compound, comprising: a squarylium compoundrepresented by Chemical Formula 1:

wherein, in Chemical Formula 1, X¹ and X² are each independently one ofa functional group represented by Chemical Formula 1A, a functionalgroup represented by Chemical Formula 1B, a functional group representedby Chemical Formula 1C, and a functional group represented by ChemicalFormula 1D, at least one of X¹ and X² is the functional grouprepresented by Chemical Formula 1A or the functional group representedby Chemical Formula 1B,

wherein, in Chemical Formula 1A, one of Y¹ and Y² is N and another of Y¹and Y² is NR¹⁶, R¹¹ and R¹² are linked with each other to collectivelycomprise a fused ring with a quinazoline ring, or R¹¹ and R¹² are eachindependently one of a first set of monovalent groups, the first set ofmonovalent groups including hydrogen, a halogen, a cyano group, a nitrogroup, a hydroxyl group, a carboxyl group, an ester group, a substitutedor unsubstituted C1 to C20 alkyl group, a substituted or unsubstitutedC1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 arylgroup, a substituted or unsubstituted C3 to C20 cycloalkyl group, asubstituted or unsubstituted C3 to C20 heteroaryl group, and asubstituted or unsubstituted C2 to C20 heterocycloalkyl group, R¹³ isone of a second set of monovalent groups, the second set of monovalentgroups including a substituted or unsubstituted C6 to C30 aryl group, asubstituted or unsubstituted C3 to C20 heteroaryl group, a substitutedor unsubstituted C6 to C20 arylamine group, and a substituted orunsubstituted C3 to C30 heteroarylamine group, and R¹⁴ and R¹⁵ arelinked with each other to collectively comprise a fused ring with aquinazoline ring, or R¹⁴, R¹⁵, and R¹⁶ are independently one ofhydrogen, a halogen, a cyano group, a nitro group, a hydroxyl group, acarboxyl group, an ester group, a substituted or unsubstituted C1 to C20alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, asubstituted or unsubstituted C6 to C30 aryl group, a substituted orunsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstitutedC3 to C20 heteroaryl group, and a substituted or unsubstituted C2 to C20heterocycloalkyl group,

wherein, in Chemical Formula 1B, m is 1 or 2, Z¹ and Z² areindependently one of hydrogen or a hydroxyl group, R²¹ to R²⁶ areindependently one of the first set of monovalent groups, and R²⁷ and R²⁸are linked with each other to collectively comprise an N-containingaromatic ring group or an N-containing alicyclic cyclic group, or R²⁷and R²⁸ are independently one of a third set of monovalent groups, thethird set of monovalent groups including a substituted or unsubstitutedC1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxygroup, a substituted or unsubstituted C6 to C30 aryl group, asubstituted or unsubstituted C3 to C20 cycloalkyl group, a substitutedor unsubstituted C3 to C20 heteroaryl group, and a substituted orunsubstituted C2 to C20 heterocycloalkyl group,

wherein, in Chemical Formula 1C, n is 1 or 2, R³¹ and R³² are linkedwith each other to collectively comprise an aromatic ring group or analicyclic cyclic group, R³³ and R³⁴ are linked with each other tocollectively comprise an aromatic ring group or an alicyclic cyclicgroup, and R³⁵ to R³⁸ are independently one of the first set ofmonovalent groups,

wherein, in Chemical Formula 1D, k is 0 or 1, Z³ and Z⁴ areindependently one of hydrogen or a hydroxyl group, R⁴¹ and R⁴² areindependently one of the first set of monovalent groups, and R⁴³ and R⁴⁴are linked with each other to collectively comprise an N-containingaromatic ring group or an N-containing alicyclic cyclic group, or R⁴³and R⁴⁴ are independently one of a substituted or unsubstituted C1 toC20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group,a substituted or unsubstituted C6 to C30 aryl group, a substituted orunsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstitutedC3 to C20 heteroaryl group, or a substituted or unsubstituted C2 to C20heterocycloalkyl group, wherein when X¹ and X² are each independently afunctional group represented by Chemical Formula 1A, R¹³ in ChemicalFormula 1A is one of a substituted or unsubstituted C6 to C30 arylgroup, a substituted or unsubstituted C3 to C20 heteroaryl group, asubstituted or unsubstituted C6 to C20 arylamine group, and asubstituted or unsubstituted C3 to C30 heteroarylamine group, whereinthe substituted or unsubstituted C3 to C20 heteroaryl group in R¹³ isone of a pyridyl group, a substituted or unsubstituted pyrazinyl group,a substituted or unsubstituted pyrimidinyl group, a substituted orunsubstituted pyridazinyl group, a substituted or unsubstitutedisoquinolyl group, a substituted or unsubstituted phthalazinyl group, asubstituted or unsubstituted quinazolinyl group, a substituted orunsubstituted quinoxalinyl group, a substituted or unsubstitutednaphthyridinyl group, a substituted or unsubstituted cinnolinyl group, asubstituted or unsubstituted pyrrolyl group, a substituted orunsubstituted pyrazolyl group, a substituted or unsubstituted imidazolylgroup, a substituted or unsubstituted triazolyl group, a substituted orunsubstituted tetrazolyl group, a substituted or unsubstituted thienylgroup, a substituted or unsubstituted thiazolyl group, a substituted orunsubstituted oxazolyl group, a substituted or unsubstituted indolylgroup, a substituted or unsubstituted isoindolyl group, a substituted orunsubstituted indazolyl group, a substituted or unsubstitutedbenzoimidazolyl group, a substituted or unsubstituted benzotriazolylgroup, a substituted or unsubstituted benzothiazolyl group, asubstituted or unsubstituted benzooxazolyl group, a substituted orunsubstituted carbazole group, a substituted or unsubstituted phenazinylgroup, and a substituted or unsubstituted acridinyl group.
 2. Thecompound of claim 1, wherein R¹¹ and R¹² of Chemical Formula 1A arelinked with each other, such that R¹¹ and R¹² collectively comprise a C6or C7 aromatic ring fused with a quinazoline ring and the C6 or C7aromatic ring does not include a heteroatom.
 3. The compound of claim 1,wherein the functional group represented by Chemical Formula 1A is afunctional group represented by Chemical Formula 1A-1:

wherein, in Chemical Formula 1A-1, one of Y¹ and Y² is N and another ofY¹ and Y² is NR¹⁶, wherein R¹⁶ is one of hydrogen or a substituted orunsubstituted C1 to C6 alkyl group, R¹⁷, R¹⁸, and R¹⁹ are independentlyone of the first set of monovalent groups, R¹³ is one of the second setof monovalent groups, and R¹⁴ and R¹⁵ are linked with each other tocollectively comprise a ring fused with a quinazoline ring, or R¹⁴ andR¹⁵ are independently one of the first set of monovalent groups.
 4. Thecompound of claim 1, wherein R¹³ of Chemical Formula 1A is one of asubstituted or unsubstituted phenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted anthracenylgroup, a substituted or unsubstituted phenanthrenyl group, a substitutedor unsubstituted pyrenyl group, a substituted or unsubstituted chrysenylgroup, a substituted or unsubstituted fluorenyl group, or a substitutedor unsubstituted perylenyl group.
 5. The compound of claim 1, whereinwhen one of X1 and X2 is a functional group represented by ChemicalFormula 1A, R¹³ of Chemical Formula 1A is one functional group of aplurality of functional groups represented by Chemical Formula 2:

wherein, in Chemical Formula 2, each position of a plurality of aromaticrings of the plurality of functional groups that is not indicated by anasterisk (*) is a binding position at R¹³ of Chemical Formula 1A.
 6. Thecompound of claim 1, wherein R¹³ of Chemical Formula 1A is one of asubstituted or unsubstituted pyrrolidinyl group, a substituted orunsubstituted piperidinyl group, a substituted or unsubstitutedpiperazinyl group, a substituted or unsubstituted morpholinyl group, asubstituted or unsubstituted thiomorpholinyl group, a substituted orunsubstituted tetrahydropyridyl group, a substituted or unsubstitutedtetrahydroquinolinyl group, a substituted or unsubstitutedtetrahydroisoquinolinyl group, a substituted or un substitutedtetrahydrofuryl group, a substituted or unsubstituted tetrahydropyranylgroup, a substituted or unsubstituted dihydrobenzofuranyl group, asubstituted or unsubstituted indolinyl group, a substituted orunsubstituted isoindolinyl group, or a substituted or unsubstitutedtetrahydrocarbazolyl group.
 7. The compound of claim 1, wherein, inChemical Formula 1A, R¹³ is one of the substituted or unsubstituted C6to C20 arylamine group or the substituted or unsubstituted C3 to C30heteroarylamine group, and the substituted or unsubstituted C6 to C20arylamine group or the substituted or unsubstituted C3 to C30heteroarylamine group is represented by —NR^(x)R^(y) wherein R^(x) andR^(y) are independently one of a substituted or unsubstituted C6 to C30aryl group and a substituted or unsubstituted C3 to C20 heteroarylgroup.
 8. The compound of claim 1, wherein Chemical Formula 1B onefunctional group of a plurality of functional groups represented byChemical Formula 1B-1, Chemical Formula 1B-2, and Chemical Formula 1B-3:

wherein, in Chemical Formula 1B-1, m is 1 or 2, Z¹ and Z² areindependently hydrogen or a hydroxyl group, R²¹ to R²⁶ are independentlyone of the first set of monovalent groups, R^(a) and R^(b) areindependently one of the first set of monovalent groups, and a and b areindependently an integer that is inclusively between 0 to 5,

wherein, in Chemical Formula 1B-2, m is 1 or 2, Z¹ and Z² areindependently one of hydrogen or a hydroxyl group, R²¹ to R²⁶ areindependently one of the first set of monovalent groups, R^(a) and R^(b)are independently one of the first set of monovalent groups, and a and bare independently an integer that is inclusively between 0 to 4,

wherein, in Chemical Formula 1B-3, m is 1 or 2, Z¹ and Z² areindependently one of hydrogen or a hydroxyl group, R²¹ to R²⁶ areindependently one of the first set of monovalent groups, R^(a) and R^(b)are independently one of the first set of monovalent groups, Y is one offrom NR^(c), O, S, Se, or Te, wherein R^(c) is one of hydrogen and asubstituted or unsubstituted C1 to C6 alkyl group, and a and b areindependently an integer that is inclusively between 0 to
 4. 9. Thecompound of claim 1, wherein Chemical Formula 1C is one functional groupof a plurality of functional groups represented by Chemical Formula 1C-1and Chemical Formula 1C-2:

wherein, in Chemical Formula 1C-1 and Chemical Formula 1C-2, R^(a),R^(b), R^(c), and R^(d) are independently one of the first set ofmonovalent groups, a and b are independently an integer that isinclusively between 0 to 6, c is an integer that is inclusively between0 to 2, and e is an integer that is inclusively between 0 to
 3. 10. Thecompound of claim 1, wherein Chemical Formula 1D is one functional groupof a plurality of functional groups represented by Chemical Formula1D-1, Chemical Formula 1D-2, and Chemical Formula 1D-3:

wherein, in Chemical Formula 1D-1, k is 0 or 1, Z³ and Z⁴ areindependently one of hydrogen or a hydroxyl group, R⁴¹ and R⁴² areindependently one of the first set of monovalent groups, R^(a) and R^(b)are independently one of the first set of monovalent groups, and a and hare independently an integer that is inclusively between 0 to 5;

wherein, in Chemical Formula 1D-2 and Chemical Formula 1D-3, k is 0 or1, Z³ and Z⁴ are independently one of hydrogen or a hydroxyl group, R⁴¹and R⁴² are independently one the first set of monovalent groups, R^(a)and R^(b) are independently one the first set of monovalent groups, Y isone of NR^(c), O, S, Se, and Te, wherein R^(c) is one of hydrogen and asubstituted or unsubstituted C1 to C6 alkyl group, and a and b areindependently an integer that is inclusively between 0 to
 4. 11. Thecompound of claim 1, wherein the squarylium compound is a particularcompound represented by one chemical formula of Chemical Formula 4-1,Chemical Formula 4-3, Chemical Formula 4-4, Chemical Formula 4-5,Chemical Formula 4-6, Chemical Formula 4-7, Chemical Formula 4-8,Chemical Formula 4-9, and Chemical Formula 4-10:

wherein, in Chemical Formula 4-1, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(14′),R^(15′), R^(16′), R^(17′), R^(18′), R^(19′), R^(p), and R^(p′) areindependently one of the first set of monovalent groups, and p and p′are independently an integer that is inclusively between 0 to 4,

wherein, in Chemical Formula 4-3, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(14′),R^(15′), R^(16′), R^(17′), R^(18′), R^(19′), R^(p), R^(p′), R^(q), andR^(q′) are independently one of the first set of monovalent groups, andp and p′ are independently an integer that is inclusively between 0 to4,

wherein, in Chemical Formula 4-4, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(p),R^(r), and R^(s) are independently one of the first set of monovalentgroups, p is an integer that is inclusively between 0 to 4, and r and sare independently an integer that is inclusively between 0 to 5,

wherein, in Chemical Formula 4-5, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(p),R^(q), and R^(s) are independently one of the first set of monovalentgroups, p is an integer that is inclusively between 0 to 4, q is aninteger that is inclusively between 0 to 2, and r and s areindependently an integer that is inclusively between 0 to 5,

wherein, in Chemical Formula 4-6, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R_(p),R^(q), R^(r), and R^(s) are independently one of the first set ofmonovalent groups, p is an integer that is inclusively between 0 to 4, qis an integer that is inclusively between 0 to 2, and r and s areindependently an integer that is inclusively between 0 to 5,

wherein, in Chemical Formula 4-7, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(p),R^(r), R^(s), and R^(w) are independently one the first set ofmonovalent groups, p and w are independently an integer that isinclusively between 0 to 4, and r and s are independently an integerthat is inclusively between 0 to 5,

wherein, in Chemical Formula 4-8, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(p),R^(q), R^(r), R^(s), R^(w) are independently one of the first set ofmonovalent groups, p and w are independently an integer that isinclusively between 0 to 4, q is an integer that is inclusively between0 to 2, and r and s are independently an integer that is inclusivelybetween 0 to 5,

wherein, in Chemical Formula 4-9, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R^(p),R^(q), R^(r), R^(s) and R^(w) are independently one of the first set ofmonovalent groups, p and w are independently an integer that isinclusively between 0 to 4, and r and s are independently an integerthat is inclusively between 0 to
 5. 12. The compound of claim 1, whereinthe squarylium compound is a particular compound represented by ChemicalFormula 4-10:

wherein, in Chemical Formula 4-10, R^(r), R^(s), R^(w), R^(r′), R^(s′),and R^(w′) are independently one the first set of monovalent groups, wand w′ are independently an integer that is inclusively between 0 to 4,and r, s, r′, and s′ are independently an integer that is inclusivelybetween 0 to
 5. 13. The compound of claim 1, wherein the squaryliumcompound is configured to have a maximum absorption wavelength (λ_(max))in a range of greater than or equal to about 700 nm and less than orequal to about 1300 rim based on the squarylium compound being in a thinfilm state.
 14. The compound of claim 1, wherein the squarylium compoundhas a full width at half maximum (FWHM) of at least about 50 nm and lessthan or equal to about 150 nm based on the squarylium compound being ina thin film state.
 15. The compound of claim 1, wherein the squaryliumcompound is associated with a maximum absorption coefficient in aninfrared ray (IR) wavelength spectrum of light (A_(NIR)) and a maximumabsorption coefficient in a visible wavelength spectrum of light(A_(VIS)) that satisfy Relationship Equation 1:A _(NIR) /A _(VIS)≥8  [Relationship Equation 1].
 16. The compound ofclaim 15, wherein A_(NIR)/A_(VIS) is in a range of about 10 to about550.
 17. An infrared cut film comprising the compound of claim
 1. 18. Aninfrared cut filter comprising: the infrared cut film of claim 17; andan infrared light reflection layer on at least one surface of theinfrared cut film.
 19. The infrared cut filter of claim 18, wherein theinfrared light reflection layer includes an inorganic particulate. 20.The infrared cut filter of claim 18, wherein the infrared lightreflection layer is a multi-layered thin film including a firstdeposition film and a second deposition film, the first deposition filmincluding an inorganic particulate that is at least one particulate oftitania (TiO₂) and zirconia, the second deposition film including aninorganic particulate that is at least one particulate of silica (SiO₂)and alumina.
 21. The infrared cut filter of claim 18, wherein athickness of the infrared cut film is in a range of about 50 μm to about200 μm.
 22. An electronic device comprising the compound of claim
 1. 23.An electronic device comprising the infrared cut film of claim
 17. 24.An electronic device comprising the infrared cut filter of claim
 18. 25.The electronic device of claim 22, wherein the electronic device is animage sensor including a first photo-sensing device configured to senselight in a blue wavelength spectrum of light, a second photo-sensingdevice configured to sense light in a red wavelength spectrum of light,a third photo-sensing device configured to sense light in a greenwavelength spectrum of light, and a fourth photo-sensing deviceconfigured to sense light in an infrared/near infrared wavelengthspectrum of light, wherein the fourth photo-sensing device includes thesquarylium compound.
 26. The electronic device of claim 25, wherein thefourth photo-sensing device is on the first photo-sensing device, thesecond photo-sensing device, and the third photo-sensing device, whereinat least two devices of the first photo-sensing device, the secondphoto-sensing device, and the third photo-sensing device are stacked.27. The electronic device of claim 25, wherein the first photo-sensingdevice and the second photo-sensing device extend in parallel to eachother, the third photo-sensing device is on the first photo-sensingdevice and the second photo-sensing device, and the fourth photo-sensingdevice is on the third photo-sensing device.
 28. The electronic deviceof claim 25, wherein the image sensor includes a blue filter on thefirst photo-sensing device, a red filter on the second photo-sensingdevice, a green filter on the third photo-sensing device, and aninfrared cut filter configured to selectively absorb light in theinfrared/near infrared wavelength spectrum of light on the fourthphoto-sensing device.
 29. The electronic device of claim 28, wherein theinfrared cut filter is on the blue filter, the red filter, and the greenfilter.